Methyl chloroformate → 6-[(cyclopropylmethyl)(propyl)amino]-N-{4-[(2-oxo-1,3-oxazolidin-4-yl)methyl]phenyl}pyrimidine-4-carboxamide

HRID 1946830Notes

Reaction equation

HRID 1946830 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.[O:32]=[C:33]1[NH:37][CH:36]([CH2:38][C:39]2[CH:45]=[CH:44][C:42]([NH2:43])=[CH:41][CH:40]=2)[CH2:35][O:34]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:43][C:42]3[CH:41]=[CH:40][C:39]([CH2:38][CH:36]4[CH2:35][O:34][C:33](=[O:32])[NH:37]4)=[CH:45][CH:44]=3)=[O:14])[CH:7]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 11842283(R)-4-(4-Aminobenzyl)-2-oxazolidinoneHCID 594470006-[(Cyclopropylmethyl)(propyl)amino]pyrimidine-4-carboxylic acid2×

Product 1

HCID 594470266-[(cyclopropylmethyl)(propyl)amino]-N-{4-[(2-oxo-1,3-oxazolidin-4-yl)methyl]phenyl}pyrimidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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, 4-[(2-oxo-1,3-oxazolidin-4-yl)methyl]aniline (Specs, 130 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

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

Sources & evidence

ORD record
ord-812b2a88ac474bea90a6ad9f09ca7656
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Reaction notes

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