N-(1H-benzimidazol-2-ylmethyl)-N-(2,2-dimethoxyethyl)-4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxamide → 6-(1H-benzimidazol-2-ylmethyl)-3-(2,4,6-trifluorobenzoyl)-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

HRID 908253Notes

Reaction equation

HRID 908253 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([CH2:30][CH:31](OC)OC)[C:12]([C:14]1[NH:15][CH:16]=[C:17]([C:19](=[O:29])[C:20]2[C:25]([F:26])=[CH:24][C:23]([F:27])=[CH:22][C:21]=2[F:28])[CH:18]=1)=[O:13]>CC#N.O>[NH:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[C:2]1[CH2:10][N:11]1[CH:30]=[CH:31][C:18]2[C:17]([C:19](=[O:29])[C:20]3[C:21]([F:28])=[CH:22][C:23]([F:27])=[CH:24][C:25]=3[F:26])=[CH:16][NH:15][C:14]=2[C:12]1=[O:13]

Participants

3

Reactant 1

HCID 58024795N-(1H-benzimidazol-2-ylmethyl)-N-(2,2-dimethoxyethyl)-4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxamide

Product 1

HCID 445486026-(1H-benzimidazol-2-ylmethyl)-3-(2,4,6-trifluorobenzoyl)-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-oneYield 52.4%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A methanesulofonic acid 1.5 mL solution of the product from Step B (910 mg, 1.87 mmol) was stirred at 95° C. in an oil bath for 25 min. The reaction mixture was cooled to room temperature, diluted with MeCN—H2O (2:3) mixture (3 mL). The resulting solution was purified by reverse phase HPLC (C-18 column) (eluent: gradient mixture of acetonitrile-water with 0.5% TFA) to give the title compound (414 mg). LC/MS: m/z 423(M+H). 1H-NMR (d6-DMSO, 500 MHz): δ 5.59 (s, 2H), 7.06 (d, 1H), 7.35-7.39 (m, 4H), 7.61-7.68 (m, 3H), 7.93 (d, 1H), 13.14 (s, 1H).

Workup

  1. customThe resulting solution was purified by reverse phase HPLC (C-18 column) (eluent: gradient mixture of acetonitrile-water with 0.5% TFA)

Sources & evidence

ORD record
ord-f9f34b157b824b53b0bca23330d4fa90
Source dataset
uspto-grants-2011_09
Patent number
US08017605B2

Reaction notes

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