Methyl chloroformate → 6-[(cyclopropylmethyl)(propyl)amino]-N-[3-(2-methyl-1H-imidazol-1-yl)phenyl]pyrimidine-4-carboxamide

HRID 1746802Notes

Reaction equation

[CH:1]1([CH2:4][N:5]([CH2:15][CH2:16][CH3:17])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([OH:14])=O)[CH:7]=2)[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.ClC(OC)=O.[CH3:32][C:33]1[N:34]([C:38]2[CH:39]=[C:40]([CH:42]=[CH:43][CH:44]=2)[NH2:41])[CH:35]=[CH:36][N:37]=1>C(Cl)Cl>[CH:1]1([CH2:4][N:5]([CH2:15][CH2:16][CH3:17])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([NH:41][C:40]3[CH:42]=[CH:43][CH:44]=[C:38]([N:34]4[CH:35]=[CH:36][N:37]=[C:33]4[CH3:32])[CH:39]=3)=[O:14])[CH:7]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

A cooled (0° C.) solution of 6-(cyclopropylmethyl(propyl)amino)pyrimidine-4-carboxylic acid (Intermediate 21, 112 mg; 0.45 mmol) in DCM was treated with diisopropylethylamine (78.4 mL; 0.52 mmol) and methyl chloroformate (36.2 mL; 0.47 mmol). After stirring at 0° C. for 15 minutes, 3-(2-methyl-1H-imidazol-1-yl)aniline (Maybridge, 117 mg; 0.67 mmol) was added and the mixture stirred for 72 hours. The solvent was evaporated and the compound purified by preparative HPLC to give the title compound as a white solid.

Workup

stirringthe mixture stirred for 72 hours
customThe solvent was evaporated
customthe compound purified by preparative HPLC

Sources & evidence

ORD record: ord-aced5314e8684daab3f0068acc32130e
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150519B2

Reaction notes

Loading…