Lithium hydroxide, monohydrate → 2-Methyl-6-{[2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy}benzo[b]thiophene-3-carboxylic acid

HRID 985320Notes

Reaction equation

HRID 985320 reaction equation
[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[N:22]([CH3:26])[CH:23]=[CH:24][N:25]=5)[S:20][C:13]=34)[CH:9]=[CH:10][C:4]=2[C:3]=1[C:27]([O:29]C)=[O:28].O[Li].O>>[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[N:22]([CH3:26])[CH:23]=[CH:24][N:25]=5)[S:20][C:13]=34)[CH:9]=[CH:10][C:4]=2[C:3]=1[C:27]([OH:29])=[O:28]

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22143653HCID 22143653, compound

Product 1

HCID 221435462-Methyl-6-{[2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy}benzo[b]thiophene-3-carboxylic acidYield 85.1%

Procedure

This material was prepared by the reaction of methyl 2-methyl-6-{[2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy}benzo[b]thiophene-3-carboxylate 117a (200 mg, 0.46 mmole) with LiOH.H2O (192 mg, 4.6 mmole) in a manner as previously described for example 11c to give a yellow solid (165 mg, 85%). 1H NMR (DMSO-d6, 300 MHz): δ8.57 (1H, d, J=5.46 Hz), 8.45 (1H, d, J=8.85 Hz), 8.00 (2H, s), 7.53 (1H, s), 7.40 (1H, dd, J=2.35, 8.95 Hz), 7.22 (1H, s), 6.79 (1H, d, J=5.46 Hz), 4.00 (3H, s), 2.82 (3H, s).

Sources & evidence

ORD record
ord-d285e2225b434172bae2a16304c2baf6
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

Loading…