1-Benzofuran-4-carboxylic acid → N-(((1S,3aS,7aS)-2-(2-Methyl-5-phenylthiazole-4-carbonyl)octahydro-1H-isoindol-1-yl)methyl)benzofuran-4-carboxamide

HRID 60839Notes

Reaction equation

HRID 60839 reaction equation
[NH2:1][CH2:2][CH:3]1[CH:11]2[CH:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)[CH2:5][N:4]1[C:12]([C:14]1[N:15]=[C:16]([CH3:25])[S:17][C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:13].[O:26]1[C:30]2=[CH:31][CH:32]=[CH:33][C:34]([C:35](O)=[O:36])=[C:29]2[CH:28]=[CH:27]1>>[CH3:25][C:16]1[S:17][C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:14]([C:12]([N:4]2[CH2:5][C@@H:6]3[C@H:11]([CH2:10][CH2:9][CH2:8][CH2:7]3)[C@H:3]2[CH2:2][NH:1][C:35]([C:34]2[CH:33]=[CH:32][CH:31]=[C:30]3[O:26][CH:27]=[CH:28][C:29]=23)=[O:36])=[O:13])[N:15]=1

Participants

3

Reactant 2

HCID 223241171-Benzofuran-4-carboxylic acidHCID 89740373(1-(aminomethyl)-1H-isoindol-2(3H,3aH,4H,5H,6H,7H,7aH)-yl)(2-methyl-5-phenylthiazol-4-yl)methanone

Product 1

HCID 89748223N-(((1S,3aS,7aS)-2-(2-Methyl-5-phenylthiazole-4-carbonyl)octahydro-1H-isoindol-1-yl)methyl)benzofuran-4-carboxamide

Procedure

The pair of stereo isomers Examples 70 and 71 were isolated by preparative HPLC from the coupling reaction according general procedure A (1-(aminomethyl)-1H-isoindol-2(3H,3aH,4H,5H,6H,7H,7aH)-yl)(2-methyl-5-phenylthiazol-4-yl)methanone and benzofuran-4-carboxylic acid. The assignment of stereochemistry is not verified. MS (ESI) 500 (M+H).

Workup

  1. customThe pair of stereo isomers Examples 70 and 71 were isolated by preparative HPLC from the coupling reaction

Sources & evidence

ORD record
ord-4eb2f2ce882149069ff57ae22486f3b8
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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