Sodium hydride → HCID 46916821, compound

HRID 1623088Notes

Reaction equation

HRID 1623088 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:6][CH:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:4][C:3]1=[O:13].[H-].[Na+].O[CH2:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][C:23]3[CH2:40][C@:30]4([C:38]5[C:33](=[N:34][CH:35]=[CH:36][CH:37]=5)[NH:32][C:31]4=[O:39])[CH2:29][C:24]=3[CH:25]=2)[N:20]=1>CN(C=O)C>[CH3:1][C:2]1([CH3:14])[CH2:6][CH:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]([CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][C:23]4[CH2:40][C@:30]5([C:38]6[C:33](=[N:34][CH:35]=[CH:36][CH:37]=6)[NH:32][C:31]5=[O:39])[CH2:29][C:24]=4[CH:25]=3)[N:20]=2)[C:3]1=[O:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 58044825HCID 58044825, compound2×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 46916821HCID 46916821, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (±)-3,3-dimethyl-5-phenylpyrrolidin-2-one (221 mg, 0.893 mmol, described in Intermediate 51) 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 7) 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 CH2Cl2: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 CH2Cl2

Sources & evidence

ORD record
ord-0e80a5ed302c4796b6c7c0478179ee3e
Source dataset
uspto-grants-2014_07
Patent number
US08778957B2

Reaction notes

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