Trifluoroacetic acid → 1-(4-(2-Amino-4-methylthiazol-5-yl)pyridin-2-yl)cyclopropanecarbonitrile

HRID 2370368Notes

Reaction equation

HRID 2370368 reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][C:10]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([C:20]3([C:23]#[N:24])[CH2:22][CH2:21]3)[CH:15]=2)=[C:11]([CH3:13])[N:12]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[S:9][C:10]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([C:20]3([C:23]#[N:24])[CH2:22][CH2:21]3)[CH:15]=2)=[C:11]([CH3:13])[N:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59293730{5-[2-(1-Cyano-cyclopropyl)-pyridin-4-yl]-4-methyl-thiazol-2-yl}-carbamic acid tert-butyl ester

Product 1

HCID 592936441-(4-(2-Amino-4-methylthiazol-5-yl)pyridin-2-yl)cyclopropanecarbonitrileYield 85.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of {5-[2-(1-cyano-cyclopropyl)-pyridin-4-yl]-4-methyl-thiazol-2-yl}-carbamic acid tert-butyl ester (Step 18.2) (295 mg), DCM (4 mL) and TFA (1 mL) is stirred for 2 h at rt and then concentrated. The residue is purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1) to afford 182 mg of the title compound: ESI-MS: 257.1 [M+H]+; tR=2.54 min (System 1); TLC: Rf=0.30 ((DCM/MeOH/NH3aq, 94:5:1).

Workup

  1. concentrationconcentrated
  2. customThe residue is purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1)

Sources & evidence

ORD record
ord-27eda01700484fd2ad8ce3e4af670892
Source dataset
uspto-grants-2014_04
Patent number
US08710085B2

Reaction notes

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