Trifluoroacetic acid → 2-Amino-4-(4-cyclopropylcarbamoyl-phenyl)-thiazole-5-carboxylic acid methyl ester

HRID 737201Notes

Reaction equation

HRID 737201 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([NH:10]C(OC(C)(C)C)=O)=[N:7][C:6]=1[C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:29])[NH:25][CH:26]2[CH2:28][CH2:27]2)=[CH:20][CH:19]=1)=[O:4].C(O)(C(F)(F)F)=O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([NH2:10])=[N:7][C:6]=1[C:18]1[CH:19]=[CH:20][C:21]([C:24](=[O:29])[NH:25][CH:26]2[CH2:28][CH2:27]2)=[CH:22][CH:23]=1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866164462-tert-Butoxycarbonylamino-4-(4-cyclopropylcarbamoyl-phenyl)-thiazole-5-carboxylic acid methyl ester

Product 1

HCID 866164452-Amino-4-(4-cyclopropylcarbamoyl-phenyl)-thiazole-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-tert-Butoxycarbonylamino-4-(4-cyclopropylcarbamoyl-phenyl)-thiazole-5-carboxylic acid methyl ester (0.28 g, 6.71 mmol) and TFA (5 mL) in dichloromethane (5 mL) was stirred at room temperature for 2 h. The mixture was concentrated in vacuo to give 2-Amino-4-(4-cyclopropylcarbamoyl-phenyl)-thiazole-5-carboxylic acid methyl ester; MS: 417.1 (M+H+).

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-f0b67a365fbf486e830e0c7007fe3db9
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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