1-Methylindole-3-carboxylic acid → 1-methyl-1H-indole-3-carboxylic acid {(1S,3S,5S)-2-[5-(3-fluoro-phenyl)-2-methyl-thiazole-4-carbonyl]-2-aza-bicyclo[3.1.0]hex-3-ylmethyl}-amide

HRID 2064848Notes

Reaction equation

HRID 2064848 reaction equation
[NH2:1][CH2:2][C@@H:3]1[CH2:8][C@H:7]2[C@H:5]([CH2:6]2)[N:4]1[C:9]([C:11]1[N:12]=[C:13]([CH3:23])[S:14][C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=1)=[O:10].[CH3:24][N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([C:34](O)=[O:35])=[CH:26]1>>[F:22][C:18]1[CH:17]=[C:16]([C:15]2[S:14][C:13]([CH3:23])=[N:12][C:11]=2[C:9]([N:4]2[C@H:3]([CH2:2][NH:1][C:34]([C:27]3[C:28]4[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:25]([CH3:24])[CH:26]=3)=[O:35])[CH2:8][C@H:7]3[C@@H:5]2[CH2:6]3)=[O:10])[CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 8540401-Methylindole-3-carboxylic acidHCID 67081101[(1S,3S,5S)-3-aminomethyl-2-aza-bicyclo[3.1.0]hex-2-yl]-[5-(3-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanone

Product 1

HCID 670811861-methyl-1H-indole-3-carboxylic acid {(1S,3S,5S)-2-[5-(3-fluoro-phenyl)-2-methyl-thiazole-4-carbonyl]-2-aza-bicyclo[3.1.0]hex-3-ylmethyl}-amide

Procedure

prepared by reaction of [(1S,3S,5S)-3-aminomethyl-2-aza-bicyclo[3.1.0]hex-2-yl]-[5-(3-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanone with 1-methyl-1H-indole-3-carboxylic acid. LC-MS (basic): tR=0.88 min; [M+H]+=489.1.

Sources & evidence

ORD record
ord-ab4da379ece44b97871aef54892eda60
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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