Cesium carbonate → 6-(2-[3-Methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yloxy)-2-methylbenzofuran-3-carboxylic acid methylamide
Reaction equation
ClC1C=C[N:5]=[C:4]2C=C(C(N3CC[C@@H](OC)C3)=O)SC=12.[CH3:20][O:21][C@@H:22]1[CH2:26][CH2:25][N:24]([C:27]([C:29]2[S:37][C:36]3[C:31](=[N:32][CH:33]=[CH:34][C:35]=3[O:38][C:39]3[CH:40]=[CH:41][C:42]4[C:46]([C:47]([OH:49])=O)=[C:45]([CH3:50])S[C:43]=4[CH:51]=3)[CH:30]=2)=[O:28])[CH2:23]1.C([O-])([O-])=[O:53].[Cs+].[Cs+]>>[CH3:4][NH:5][C:47]([C:46]1[C:42]2[CH:41]=[CH:40][C:39]([O:38][C:35]3[CH:34]=[CH:33][N:32]=[C:31]4[CH:30]=[C:29]([C:27]([N:24]5[CH2:25][CH2:26][CH:22]([O:21][CH3:20])[CH2:23]5)=[O:28])[S:37][C:36]=34)=[CH:51][C:43]=2[O:53][C:45]=1[CH3:50])=[O:49]Participants
Reactant 3
Product 1
Procedure
This material was prepared by the reaction of 7-chloro-2-[(R)-3-methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridine 4b (144 mg, 0.5 mmole) with 6-hydroxy-2-methylbenzo[b]furan-3-carboxylic acid methylamide 11c (120 mg, 0.6 mmole) and Cs2CO3 (794 mg, 2.4 mmole) in a manner as previously described for example 1 to give 134 mg (59%) of an off-white solid. 1H NMR (DMSO-d6) δ 8.58 (1H, d, J=5.3 Hz), 8.07 (1H, s), 7.97 (1H, d, J=4.5 Hz), 7.83 (1H, d, J=8.6 Hz), 7.65 (1H, d, J=2.0 Hz), 7.24 (1H, dd, J=2.0, 8.6 Hz), 6.72 (1H, d, J=5.3 Hz), 4.25–3.75 (3H, m), 3.65–3.45 (2H, m), 3.27, 3.24 (3H, s), 2.82 (3H, d, J=4.3 Hz), 2.62 (3H, s), 2.15–1.95 (2H, m). Anal. Calcd for C24H23N3O5S.0.5H2O: C, 60.74; H, 5.10; N, 8.86; S, 6.76. Found: C, 60.89; H, 5.16; N, 8.69; S, 6.58.
Sources & evidence
- ORD record
- ord-3a689061692b4d94a63b5d1adc5a8fdb
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07045528B2
Reaction notes
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