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With development of on-line chemical directo-ries acquiring necessary reagents and building blocks for day-to-day research activity has be-come a technical routine. Many thousands of building blocks are now available in the market and sub-structure search can efficiently provide a selection of reagents to buy. However, this approach might be limited.

With over 100,000 building blocks synthesized and now available from our stock we are a re- cognized leader in the market. Our catalogue features versatile building block classes and adds 1,000 products each month. Although they all are available for purchase through www.enaminestore.com and many public or corporate chemical databases we wanted to gather together the most interesting and re-cently prepared building blocks to provide a series of useful guides to a novel and innova-tive chemistry.

Selected Building Block

Series

2 Fluorinated aliphatic amines

Fluorinated aliphatic amines

N

O

NN

Cl

Cl

F

F F

N

OCO2H

F

F

ClNH2N N

NC

F

O HN

N

N

N

NH

N

F F

MeO2C

MeON

N

OAc

HO CO2MeH

H

HNO2S

NN

F3C CF3

VinflunineLaboratoires Pierre Fabre, 1998

CitafloxacineDaiichi Sankyo Co., 2008

Nootropic agentMarck Research Laboratories, 2005

Antiurinary agentPfizer Inc., 2002

MelogliptinGlenmark Pharm., 2006

Motifs of fluorinated aliphatic amines are common in drug discovery.

3www.enaminestore.com

Linear amines

EN300-96615 EN300-114376

EN300-102325 EN300-74923

EN300-84693 EN300-35000

EN300-69309 EN300-32020

EN300-41781 EN300-93182

EN300-100456 EN300-94944

EN300-101814 EN300-93912

EN300-90872 EN300-40766

F

FH2NCF3

H2NO

H2N F F

F

SH2N

H2N FCF3H2N

O

F

F

H2NCF3H2N O

CF3H2NH2N

CF3

H2N

F H2NO

F3C

F

FH2N

F3CH2N

CF3H2N CF3

SH2N

HCl HCl

HCl

HCl

HCl

HCl HCl

HCl HCl

HCl HCl

https://www.enaminestore.com/catalog/EN300-96615

















NHN

N

O

HNNN

FO

CO2H

HNHN

NN

NN

NH2 HO

F3C OH

OF3C N

OOF3C

O

NO

F3CO

OHF3C NHBoc F3C NH2

94% 82%

70%

72%63%

F3C OEt

OO

F3C OEt

O

*HCl

F3C OEt

OOH

93%

94% 69%

NaBH4 P2O5

NaOH

Me3SOIEDC

MeNHOMe

t-BuOK

(PhO)2PON3 HCl

EN300-42754

Ciprofloxacin Nevirapine Abocavir

Recently we developed a practical synthesis of the novel building block: trans-2-(trifluoromethyl)-cyclopropanamine.1,2

Fragment of cyclopropanamine is common in approved drugs:

1. A. V. Bezdudny et al. Synthesis 2011, 1, 119.2. V. S. Yarmolchuk et al. Synthesis 2012, 44, 1152.

trans-2-(Trifluoromethyl)-cyclopropanamine



Exocyclic amines

EN300-42754 EN300-104701

EN300-79761 EN300-112279

EN300-74868 EN300-75524

EN300-94391 EN300-27688

EN300-78062 EN300-26926

EN300-90484 EN300-27291

EN300-115151 EN300-96312

EN300-99908 EN300-109808

CF3

H2N

FF

H2N

F3C

H2N

FF

H2N

BocHN

FF

F3C

H2N

F3C

H2N

F3C

H2N

F

FH2N

CF3

H2N

F

FH2N CF3H2N

H2N

F F C3

H2N

FF

H2N

F

FH2N

HCl HCl

HCl

HCl

HCl

HCl

HCl

HCl HCl


















N

N

NHO

FCl

NO

EN300-83298EN300-81684

NH

O

NH

O CF3

NH

O

CF3

Morpholine

NO F

N

OONHAc

NS

N N

O

O NHtBu

OH

S

N

O NO

NHCO2Et

Cl

O

NHN

O

Trifluoromethylated morpholines

Timolol Moricizine Moclobenide

Motif of morpholine is highly common in drug discovery. Many FDA-approved drugs contain morpholine moiety.

1. A. V. Shcherbatiuk et al. Tetrahedron 69 2013, 3796-3804.

Recently we developed a practical approach to trifluoromethylated mor-pholines. The trifluoromethyl substituent multidimensionally tuned the

metabolic stability, bacisity and lipophilicity of the parent structure.1

Geffitinib Linezolid


Morpholines, Piperidines and Bicyclic amines

EN300-81684 EN300-97937

EN300-90726 EN300-79100

EN300-52620 EN300-73968

EN300-83298 EN300-113369

EN300-90738 EN300-109987

EN300-110108 EN300-100245

EN300-93067 EN300-73116

EN300-113083 EN300-73117

CF3O

NH

CF3

NH

CF3O

NH

CF3

NH

O

NH

F F

FFCF3HN

CF3NH

O

HN

F

CF3NH

O

HN

FF

HN

F

F

F

F

HN

CF3HNNHN

F

HN

FF

NHN

F

F

HCl HCl

HCl

HCl

HCl HCl

HCl

HCl HCl

2HCl

HCl 2HCl


















Azetidines and Pyrrolidines

EN300-89727 EN300-100104

EN300-110434 EN300-89584

EN300-94689 EN300-89757

EN300-108152 EN300-102456

EN300-107382 EN300-109585

EN300-116702 EN300-73354

EN300-90481 EN300-79916

EN300-105150 EN300-95926

HN F HNF

F

HN

F

FNH F

F

CF3HN

NH

F

CF3

HNOH

NH

F

F

CF3

HN

NH

F

F

CO2Me

HN F

CF3

NH

HNF

F

CF3

CF3

NH

CF3HN

OH

CF3CF3

NH

HCl

HCl

HCl HCl

HCl HCl

HCl HCl

HCl HCl

HCl

HCl HCl


















Amino alcohols

EN300-51459 EN300-108152

EN300-29780 EN300-105150

EN300-84068 EN300-89625

EN300-74756 EN300-102059

EN300-111534 EN300-71887

EN300-82765 EN300-80830

EN300-112237 EN300-58599

EN300-82572 EN300-110084

CF3

OH

H2N

CF3

HNOH

CF3

OH

H2N

CF3HN

OH

CF3HN

OH

BocNCF3

OH

CF3H2N

OH

BocN

CF3

OH

CF3

OHH2N

HO

HN

CF3

CF3

OHH2N

CF3

HN

HO

CF3

OHH2N HN

CF3

OH

OHH2N

F3C CF3

HN

OH

HCl HCl

HCl HCl

HCl

HCl

HCl HCl

HCl

HCl

HCl


















NH2

CF3

CO2H

NH2

CO2H

NH2

CO2H

NH2

CO2H

Cl

Cl

Cl

ClBrBr

MeLi CF3I

NCF3

CN

Ph

ICF3

CF3

O

H

CF3

OH

OMe

CF3NH

Ph

CNOH CF3

NH

Ph

CNOH

Pb(OAc)4

NH2

CF3

CO2H

Me3SiCN

NaOH, CHBr3

pinacole70%

1) t-BuLi2) HCOOMe

62%

++

HCl

(2 steps)90%

(2 steps)

R-phenylglycinol

(2 steps)95%

CF3-Bpg, EN300-53088

19F NMR label for peptide studies

1 P. K. Mikhailiuk et al. Angew. Chem. Int. Ed. 2006, 45, 5659.2 P. K. Mykhailiuk et al. Fluorine Chem. 2010, 131, 217.3 V. S. Kubyshkin et al. in Fluorine in Pharmaceutical and Medicinal Chemistry: From Biophysical Aspects to

Clinical Applications. (Eds.: V. Gouverneur, K. Muller), Imperial College Press, London, 2012, 91.4 M. Salwiczek et al. Amino Acids 2010, 39, 1589.

Amino acid CF3-Bpg was already used to study the structure of several

membrane-active peptides:3 gramicidin S, PGLa, SAP, (KIGAKI)3, Magainin

2, Temporin A and to evaluate the coil-coiled interactions within a poly-peptide sequence.4

Fluorinated amino acid 3-(trifluoromethyl)bicyclopent-[1.1.1]-1-ylg-lycine, (CF

3-Bpg), was designed,1 synthesized1,2 and validated1 as a

19F NMR label for structure analysis of membrane active peptides. The amino acid is perfectly suited to replace the residues of Val, Ile and Leu in peptides.

Val Leu lle CF3-Bpg

natural amino acide 19F-NMR label

Synthesis:



Amino acids

EN300-65367 EN300-96908

EN300-101571 EN300-89429

EN300-53088 EN300-61407

EN300-89327 EN300-76959

EN300-110322 EN300-109585

EN300-75802 EN300-74301

EN300-34890 EN300-74493

EN300-85544 EN300-07164

NH2 F

FHO C2

NH

F

CO2H

CF3

NH2

HO C2

NBoc

FCO2H

NH2

F3C

CO2HCF3

NH

CO2H

F3CNHFmoc

CO2H

NBoc

CF3HO C2

NH

F

F

CO2H

NH

F

F

CO2Me

NH

CF3HO C2

F3C

H2NCO2H

NH

F3C

S

CO2H

F3C

H2NCO2H

F

NH2

F

CO2H

CF3

H2NCO2H

HCl

HCl

HCl

HCl HCl

HCl HCl

HCl

HCl HCl


















Diverse derivatives

EN300-93520 EN300-109961

EN300-97552 EN300-74445

EN300-116549 EN300-78514

EN300-50504 EN300-30697

EN300-40849 EN300-90523

EN300-58944 EN300-78403

EN300-67015 EN300-29977

EN300-84859 EN300-35893

OF3C

H2NCF3

H2N

H2N

F3C

O

O

H2N

CF3

NH2

H2N

CF3

NH2

CF3

NHHN

CF3

H2N

Ph

F3C

OH

H2N

CF3

OH

H2N

Ph

CF3NH

O

CF3N

Ph

CO2H

CF3NH

O

NH2

F

F

CO2HCF3

NH

O

NH2

F

F

CO2HF3C

NH

O

HCl 2HCl

2HCl

HCl 2HCl

HCl


















New Arrivals

EN300-124674 EN300-127532

EN300-156761 EN300-156956

EN300-137256 EN300-129123

EN300-123357 EN300-142149

EN300-157667 EN300-157661

EN300-160286 EN300-137379

EN300-155382 EN300-126976

EN300-126061 EN300-127298

N

F

HNH

F

N

O F

F

HNH

O F

F

N

F

H

CF3

NH

NH

F CF3

NH

CF3

NH

NH

O

CF3

NH

F

F

NH

F

NH

OF

F

NH

F FF

F

F

F

CF3

N

NH2

NH

F

HCl HCl

HCl HCl

HCl

HCl HCl

HCl

HCl HCl

HCl HCl

HCl HCl


















New Arrivals

EN300-141346 EN300-142130

EN300-142012 EN300-153048

EN300-171143 EN300-128644

EN300-171045 EN300-159776

EN300-157446 EN300-155850

EN300-172096 EN300-171923

EN300-130197 EN300-173310

EN300-132383 EN300-131174

FNH2

CF3

NH2

OH

NH2

F

BocNH NH2

F F

CF3

NH2 CF3

NH2

CO2H

CF3 NH2

O NHBoc

NH

F

CF3

NH2

NH

OH

F

F

F

F

O NH2 NH

F F

OH

CF3

O

NH2

NH

F

FOH

FF

NH2

NH

OH

CF3

HCl HCl

HCl

HCl

HCl HCl

HCl HCl


















Notes

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