Lithium hydroxide, monohydrate → 6-[(2-{[(2S)-2-(Methoxymethyl)pyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridin-7-yl)oxy]-2-methylbenzo[b]thiophene-3-carboxylic acid
Reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([C:11]1[S:19][C:18]2[C:13](=[N:14][CH:15]=[CH:16][C:17]=2[O:20][C:21]2[CH:22]=[CH:23][C:24]3[C:28]([C:29]([O:31]C)=[O:30])=[C:27]([CH3:33])[S:26][C:25]=3[CH:34]=2)[CH:12]=1)=[O:10].O[Li].O>>[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([C:11]1[S:19][C:18]2[C:13](=[N:14][CH:15]=[CH:16][C:17]=2[O:20][C:21]2[CH:22]=[CH:23][C:24]3[C:28]([C:29]([OH:31])=[O:30])=[C:27]([CH3:33])[S:26][C:25]=3[CH:34]=2)[CH:12]=1)=[O:10]Participants
3
Reactant 2
Product 1
Procedure
This material was prepared by the hydrolysis of methyl 6-[(2-{[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridin-7-yl)oxy]-2-methylbenzo[b]thiophene-3-carboxylate 122a (63 mg, 0.13 mmole) with LiOH.H2O (54 mg, 13 mmole) in a manner as previously described for example 11c to give a white solid (46 mg, 75%). 1H NMR (DMSO-d6, 300 MHz) δ8.58 (1H, d, J=5.46 Hz), 8.44 (1H, d, J=8.85 Hz), 8.03 (1H, s), 8.00 (1H, d, J=2.26 Hz), 7.38 (1H, dd, J=2.45, 9.04 Hz), 6.78 (1H, d, J=5.84 Hz), 4.35-4.25 (1H, m), 3.93-3.76 (2H, m), 3.59-3.50 (2H, m), 3.27, 3.15 (3H, s), 2.81 (3H, s), 2.11-1.83 (4H, m).
Sources & evidence
- ORD record
- ord-152451dd62364eb5b2ca1e7816d28a2b
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06869962B2
Reaction notes
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