Hydrochloric Acid → 6-[(2-{[(3R)-3-methoxypyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridin-7-yl)oxy]-2-methylbenzo[b]thiophene-3-carboxylic acid

HRID 985199Notes

Reaction equation

HRID 985199 reaction equation
[CH3:1][O:2][C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[S:18][C:17]3[C:12](=[N:13][CH:14]=[CH:15][C:16]=3[O:19][C:20]3[CH:21]=[CH:22][C:23]4[C:27]([C:28]([O:30]C)=[O:29])=[C:26]([CH3:32])[S:25][C:24]=4[CH:33]=3)[CH:11]=2)=[O:9])[CH2:4]1.COC1C=CC2C=C(C)SC=2C=1.O[Li].O.Cl>C1COCC1.CO.O.O>[CH3:1][O:2][C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[S:18][C:17]3[C:12](=[N:13][CH:14]=[CH:15][C:16]=3[O:19][C:20]3[CH:21]=[CH:22][C:23]4[C:27]([C:28]([OH:30])=[O:29])=[C:26]([CH3:32])[S:25][C:24]=4[CH:33]=3)[CH:11]=2)=[O:9])[CH2:4]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 20767770HCID 20767770, compoundHCID 221434866-Methoxy-2-methylbenzo[b]thiophene

Product 1

HCID 599907666-[(2-{[(3R)-3-methoxypyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridin-7-yl)oxy]-2-methylbenzo[b]thiophene-3-carboxylic acidYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of methyl 6-[(2-{[(3R)-3-methoxypyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridin-7-yl)oxy]-2-methylbenzo[b]thiophene-3-carboxylate 1:1b (258 mg, 0.535 mmole) in a mixture of THF/MeOH/H2O (3:2:1, 6 ml) was added LiOH.H2O (224 mg, 5.35 mmole). The reaction was stirred 24 hours at ambient temperature. The mixture was diluted with H2O (10 ml) and acidified to pH 1 with 1 M HCl. The precipitate was collected by vacuum filtration, rinsed with MeOH, and dried at 50° C. under vacuum to afford 116 mg (45%) of a pale brown solid. 1H NMR (DMSO-d6) δ8.58 (1H, d, J=5.4 Hz), 8.44 (1H, d, J=8.9 Hz), 8.07 (1H, s), 8.00 (1H, d, J=24 Hz), 7.39 (1H, dd, J=2.4, 8.9 Hz), 6.78 (1H, d, J=5.4 Hz), 4.10-3.81 (3H, m), 3.69-3.54 (4H. m), 3.27, 3.24 (3H, s), 2.81 (3H, s).

Workup

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washrinsed with MeOH
  3. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-02f39d7bdda54292b74814629b8fe360
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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