6-Chloro-1-benzothiophene-2-carboxylic acid → 3-(3-Cyanophenyl)-2-[1-(6-chlorobenzo[b]thiophene-2-carbonyl)-pyrrolidin-2-yl]-propionic acid methyl ester

HRID 901324Notes

Reaction equation

HRID 901324 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([C:10]([OH:12])=O)[S:7][C:6]=2[CH:13]=1.[CH3:14][O:15][C:16](=[O:32])[CH:17]([CH:27]1[CH2:31][CH2:30][CH2:29][NH:28]1)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[N:26])[CH:20]=1>>[CH3:14][O:15][C:16](=[O:32])[CH:17]([CH:27]1[CH2:31][CH2:30][CH2:29][N:28]1[C:10]([C:8]1[S:7][C:6]2[CH:13]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[CH:9]=1)=[O:12])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[N:26])[CH:20]=1

Participants

3

Reactant 2

HCID 71419196-Chloro-1-benzothiophene-2-carboxylic acidHCID 692529693-(3-Cyanophenyl)-2-(pyrrolidin-2-yl)-propionic acid methyl ester

Product 1

HCID 692550853-(3-Cyanophenyl)-2-[1-(6-chlorobenzo[b]thiophene-2-carbonyl)-pyrrolidin-2-yl]-propionic acid methyl esterYield 78.1%

Procedure

6-Chlorobenzo[b]thiophene-2-carboxylic acid (0.24 g, 1.14 mmol) is coupled to 3-(3-cyanophenyl)-2-(pyrrolidin-2-yl)-propionic acid methyl ester (0.295 g, 1.14 mmol) as described in EXAMPLE 1B to give 3-(3-cyanophenyl)-2-[1-(6-chlorobenzo[b]thiophene-2-carbonyl)-pyrrolidin-2-yl]-propionic acid methyl ester (0.40 g, 0.89 mmol). This material is treated and purified as described in EXAMPLE 1C to obtain the title compound (0.27 g, 0.46 mmol). NMR (DMSO-d6, 300 MHz) 9.31-9.15(m, 4H), 8.13(s, 1H), 7.95-7.85(m, 2H), 7.62-7.40(m, 5H), 4.53, 4.38(two m, 1H), 3.95-3.55(m, 2H), 3.60-3.53(m, 1H), 3.52-3.49(two s, 3H), 3.14-2.95(m, 1H), 2.94-2.80(m, 1H), 2.18-1.55(m, 4H): MS m/z: [M+H]+=470. Elemental analysis calculated with 1.0 mole of H2O: C=51.87, H=4.52, N=6.98; found C=51.93, H=4.23, N=6.75.

Sources & evidence

ORD record
ord-43e70195877e4abfa30873da6eeb0cfb
Source dataset
uspto-grants-2008_04
Patent number
US07361663B2

Reaction notes

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