Cesium carbonate → 2-Methyl-6-[2-(2-methoxymethyl-pyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-benzofuran-3-carboxylic acid isobutyl amide
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.[CH2:21]([NH:25][C:26]([C:28]1[C:32]2[CH:33]=[CH:34][C:35]([OH:37])=[CH:36][C:31]=2[O:30][C:29]=1[CH3:38])=[O:27])[CH:22]([CH3:24])[CH3:23].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH2:21]([NH:25][C:26]([C:28]1[C:32]2[CH:33]=[CH:34][C:35]([O:37][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][CH:14]5[CH2:18][O:19][CH3:20])=[O:12])[S:10][C:3]=34)=[CH:36][C:31]=2[O:30][C:29]=1[CH3:38])=[O:27])[CH:22]([CH3:24])[CH3:23]Participants
4
Reactant 3
Product 1
Procedure
This material was prepared by the reaction of 7-chloro-2-[(R)-2-methoxymethylpyrrolidine-1-carbonyl]thieno[3,2-b]pyridine 2a with 6-hydroxy-2-methyl-benzofuran-3-carboxylic acid isobutyl amide 84b and Cs2CO3 in a manner as previously described for example 1. 1H NMR (CD3CN) δ8.53 (1H, d, J=5.3 Hz), 7.87 (1H, s), 7.82 (1H, d, J=8.5 Hz), 7.41 (1H, d, J=1.9 Hz), 7.20 (1H, dd, J=8.5, 1.9 Hz), 6.70 (1H, d, J=5.5 Hz), 4.38 (1H, m), 3.85 (2H, m), 3.65-3.41 (2H, m), 3.32 (3H, s), 3.23 (2H, t, J=6.4 Hz), 2.65 (3H, s), 2.15-1.94 (4H, m, partially obscured by CD3CN), 1.73 (1H, m),.
Sources & evidence
- ORD record
- ord-6d22ac22f51545b9b0d8caa1e093bf47
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06869962B2
Reaction notes
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