Cesium carbonate → 6-(2-[(S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yloxy)-2-methylbenzo[b]thiophene-3-carboxylic acid methylamide

HRID 985190Notes

Reaction equation

HRID 985190 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:17][CH2:16][CH2:15][C@H:14]3[CH2:18][O:19][CH3:20])=[O:12])[S:10][C:3]=12.[CH3:21][NH:22][C:23]([C:25]1[C:26]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][C:27]=2[S:28][C:29]=1[CH3:30])=[O:24].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:21][NH:22][C:23]([C:25]1[C:26]2[CH:34]=[CH:33][C:32]([O:35][C:2]3[CH:7]=[CH:6][N:5]=[C:4]4[CH:8]=[C:9]([C:11]([N:13]5[CH2:17][CH2:16][CH2:15][C@H:14]5[CH2:18][O:19][CH3:20])=[O:12])[S:10][C:3]=34)=[CH:31][C:27]=2[S:28][C:29]=1[CH3:30])=[O:24]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 20767764HCID 20767764, compoundHCID 207678636-Hydroxy-n,2-dimethyl-1-benzothiophene-3-carboxamide

Product 1

HCID 599908186-(2-[(S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yloxy)-2-methylbenzo[b]thiophene-3-carboxylic acid methylamideYield 73%

Procedure

This material was prepared by the reaction of 7-chloro-2-[(S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridine 2a (153 mg, 0.5 mmole) with 6-hydroxy-2-methylbenzo[b]thiophene-3-carboxylic acid methylamide 1d (164 mg, 0.7 mmole) and Cs2CO3 (868 mg, 2.7 mmole) in a manner as previously described for example 1 to give 178 mg (73%) of a yellow solid. 1H NMR (DMSO-d6): δ8.57 (1H, d, J=5.4 Hz, 8.29 (1H, q, J=4.5 Hz), 8.02 (1H, s), 7.95 (1H, d, J=2.2 Hz), 7.85 (1H, d, J=8.8 Hz), 7.32 (1H, dd, J=2.2, 8.8 Hz), 6.75 (1H, d, J=5.4 Hz), 4.37-4.23 (1H, m), 3.95-3.74 (2H, m), 3.60-3.48 (2H, m), 3.27 (3H, s), 2.83 (3H, d, J=4.5 Hz), 2.60 (3H, s), 2.08-1.81 (4H, m). Anal. Calcd. for C25H25N3O4S2: C, 60.58; H, 5.08; N, 8.48; S, 12.94. Found: C, 60.55; H, 5.33; N, 8.27; S, 12.68.

Sources & evidence

ORD record
ord-3b96c64880824d9c9ec9bc7b9d5a1ae7
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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