Diphenylacetic Acid → 2-Diphenylacetylamino-thiazole-4-carboxylic acid ethyl ester

HRID 533971

Reaction equation

HRID 533971 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH2:10])[S:8][CH:9]=1)=[O:4].[C:11]1([CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18](O)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:27](N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[CH2:1]([O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:18](=[O:19])[CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[S:8][CH:9]=1)=[O:4])[CH3:27]

Participants

6

Reactant 4

HCID 8333Diphenylacetic AcidHCID 8471TriethylamineHCID 840099Methyl 2-amino-1,3-thiazole-4-carboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 580329622-Diphenylacetylamino-thiazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Amino-thiazole-4-carboxylic acid methyl ester (32 mg, 0.20 mmol) and diphenyl-acetic acid (42 mg, 0.20 mmol) were dissolved in N,N-dimethylformamide (1 mL) containing triethylamine (84.1 μL, 0.600 mmol). O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (84 mg, 0.22 mmol) was added and the solution was allowed to stir for 16 hours. The crude product was purified by reverse-phase preparative liquid chromatography (19 mg, 0.052 mmol, 26%). ESI-MS m/z calc. 366.1. found 367.1 (M+1)+ Retention time 3.34 minutes.

Workup

  1. customThe crude product was purified by reverse-phase preparative liquid chromatography (19 mg, 0.052 mmol, 26%)

Sources & evidence

ORD record
ord-e8c8fb1783d94335baa445a5b3716131
Source dataset
uspto-grants-2014_10
Patent number
US08853415B2

Linked notes

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