Ethanol → 4-[6-(2,4-difluorophenoxy)-2-oxo-1,3-dihydrobenzimidazol-5-yl]-6-methyl-1H-pyrrolo[2,3-c]pyridin-7-one

HRID 629297Notes

Reaction equation

[F:1][C:2]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:3]=1[O:4][C:5]1[C:14]([C:15]2[C:16]3[CH:25]=[CH:24][N:23](S(C4C=CC(C)=CC=4)(=O)=O)[C:17]=3[C:18](=[O:22])[N:19]([CH3:21])[CH:20]=2)=[CH:13][C:8]2[NH:9][C:10](=[O:12])[NH:11][C:7]=2[CH:6]=1.C(O)C.[OH-].[Na+].O>>[F:1][C:2]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:3]=1[O:4][C:5]1[C:14]([C:15]2[C:16]3[CH:25]=[CH:24][NH:23][C:17]=3[C:18](=[O:22])[N:19]([CH3:21])[CH:20]=2)=[CH:13][C:8]2[NH:9][C:10](=[O:12])[NH:11][C:7]=2[CH:6]=1

Participants

Reactant 4

HCID 702Ethanol

HCID 962Water

HCID 14798Sodium Hydroxide

HCID 1180936395-(2,4-Difluorophenoxy)-6-{6-methyl-1-[(4-methylphenyl)sulfonyl]-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 917996544-[6-(2,4-difluorophenoxy)-2-oxo-1,3-dihydrobenzimidazol-5-yl]-6-methyl-1H-pyrrolo[2,3-c]pyridin-7-oneYield 21%

Conditions

Temperature: 80 °C

Procedure

A solution of 5-(2,4-difluorophenoxy)-6-{6-methyl-1-[(4-methylphenyl)sulfonyl]-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one (0.024 g, 0.035 mmol) in ethanol (0.4 mL, 7 mmol) was treated with 1.0 M sodium hydroxide in water (0.18 mL, 0.18 mmol) and stirred at 80° C. for 30 min. Purification via preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water 0.1% ammonium hydroxide, at flow rate of 30 mL/min) gave the desired product (3 mg, 20%). 1H NMR (500 MHz, DMSO-d6) δ 11.93 (br s, 1H), 10.62 (br s, 2H), 7.34-7.26 (m, 1H), 7.22 (d, J=2.8 Hz, 1H), 7.17 (s, 1H), 7.02-6.87 (m, 3H), 6.52 (s, 1H), 6.17 (d, J=2.7 Hz, 1H), 3.50 (s, 3H); LCMS calculated for C21H15F2N4O3 (M+H)+: m/z=409.1. found: 409.1.

Workup

customPurification via preparative LCMS (XBridge C18 column
washeluting with a gradient of acetonitrile/water 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record: ord-e2537d6ce7514ca2aadb536d3269ad39
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315501B2

Reaction notes

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