Sodium hydride → 2-(5,7-Dimethyl-2-oxo-3-{[(7S)-2'-oxo-1',2',6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2-yl]methyl}-2,3-dihydro-1H-benzimidazol-1-yl)-N,N-dimethylacetamide

HRID 656843Notes

Reaction equation

HRID 656843 reaction equation
[CH3:1][C:2]1[CH:17]=[C:16]([CH3:18])[C:5]2[N:6]([CH2:10][C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[H-].[Na+].O[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][C:27]3[CH2:44][C@:34]4([C:42]5[C:37](=[N:38][CH:39]=[CH:40][CH:41]=5)[NH:36][C:35]4=[O:43])[CH2:33][C:28]=3[CH:29]=2)[N:24]=1>CN(C=O)C>[CH3:1][C:2]1[CH:17]=[C:16]([CH3:18])[C:5]2[N:6]([CH2:10][C:11]([N:13]([CH3:14])[CH3:15])=[O:12])[C:7](=[O:9])[N:8]([CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][C:27]5[CH2:44][C@:34]6([C:42]7[C:37](=[N:38][CH:39]=[CH:40][CH:41]=7)[NH:36][C:35]6=[O:43])[CH2:33][C:28]=5[CH:29]=4)[N:24]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 574571932-(5,7-Dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-N,N-dimethylacetamide2×HCID 67016575(S)-2-(Hydroxymethyl)-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one2×

Product 1

HCID 161128562-(5,7-Dimethyl-2-oxo-3-{[(7S)-2'-oxo-1',2',6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2-yl]methyl}-2,3-dihydro-1H-benzimidazol-1-yl)-N,N-dimethylacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(5,7-dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-N,N-dimethylacetamide (221 mg, 0.893 mmol, described in Intermediate 17) in DMF (0.5 mL), at ambient temperature, was added sodium hydride (60% dispersion in mineral oil; 37 mg, 0.923 mmol). The resulting mixture was stirred for 30 min, then (S)-2-(chloromethyl)-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (100 mg, 0.298 mmol, described in Intermediate 11) was added and the resulting mixture was stirred at ambient temperature for 2 h. The reaction mixture was quenched with H2O (0.1 mL) and purified directly by silica gel chromatography, eluting with a gradient of CH2 Cl2:MeOH—100:0 to 95:5, to give the title compound. MS: m/z=547 (M+1). HRMS: m/z=547.2466; calculated m/z=547.2452 for C32H31N6O3.

Workup

  1. stirringthe resulting mixture was stirred at ambient temperature for 2 h
  2. customThe reaction mixture was quenched with H2O (0.1 mL)
  3. custompurified directly by silica gel chromatography
  4. washeluting with a gradient of CH2 Cl2

Sources & evidence

ORD record
ord-d6016117eaf1457bad634a2244fbfcbc
Source dataset
uspto-grants-2011_12
Patent number
US08071772B2

Reaction notes

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