Methyl 2-amino-1,3-thiazole-4-carboxylate → 2-(5-methyl-2-phenyl-4,5,6,7-tetrahydro-1H-indol-1-yl)-1,3-thiazole-4-carboxylic acid

HRID 2064559Notes

Reaction equation

HRID 2064559 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][C:5](=O)[CH:4]([CH2:9][C:10](=O)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3]1.[NH2:18][C:19]1[S:20][CH:21]=[C:22]([C:24]([O:26]C)=[O:25])[N:23]=1>>[CH3:1][CH:2]1[CH2:7][CH2:6][C:5]2[N:18]([C:19]3[S:20][CH:21]=[C:22]([C:24]([OH:26])=[O:25])[N:23]=3)[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][C:4]=2[CH2:3]1

Participants

3

Reactant 2

HCID 840099Methyl 2-amino-1,3-thiazole-4-carboxylateHCID 122703404-Methyl-2-(2-oxo-2-phenylethyl)cyclohexanone

Product 1

HCID 592146382-(5-methyl-2-phenyl-4,5,6,7-tetrahydro-1H-indol-1-yl)-1,3-thiazole-4-carboxylic acidYield 49%

Procedure

Following the general methods as outlined under Intermediate 13, starting from 4-methyl-2-(2-oxo-2-phenylethyl)cyclohexanone and methyl 2-amino-1,3-thiazole-4-carboxylate, the title compound was isolated in 49% yield (93% purity by HPLC). MS(ESI+): 339.5; MS(ESI−): 337.4.

Sources & evidence

ORD record
ord-682deb42fa5a418a8fc5e4aa83b7b0d1
Source dataset
uspto-grants-2012_10
Patent number
US08288432B2

Reaction notes

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