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Sodium hydride → 2-chloro-4-{[(3S)-1-methyl-5-oxo-3-pyrrolidinyl][(2-methylphenyl)methyl]amino}benzonitrile

HRID 1160415
Notes
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Reaction equation

HRID 1160415 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:11]=[C:10]([NH:12][C@H:13]2[CH2:17][C:16](=[O:18])[N:15]([CH3:19])[CH2:14]2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7].I[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:28].[NH4+].[Cl-]>CN(C=O)C.C(OCC)C>[Cl:3][C:4]1[CH:11]=[C:10]([N:12]([C@H:13]2[CH2:17][C:16](=[O:18])[N:15]([CH3:19])[CH2:14]2)[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 6390381-(Iodomethyl)-2-methylbenzeneHCID 595161672-Chloro-4-{[(3S)-1-methyl-5-oxo-3-pyrrolidinyl]amino}benzonitrile

Product 1

HCID 241783932-chloro-4-{[(3S)-1-methyl-5-oxo-3-pyrrolidinyl][(2-methylphenyl)methyl]amino}benzonitrileYield 76.3%

Reagents, catalysts & solvents

2
HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

NaH (60% in mineral oil, 0.857 g, 21.4 mmol) was washed with pet ether (3×), suspended in DMF (50 mL), and cooled to 0° C. To this suspension was added a solution of 2-chloro-4-{[(3S)-1-methyl-5-oxo-3-pyrrolidinyl]amino}benzonitrile (5.08 g, 20.0 mmol) and DMF (25 mL) dropwise over 20 min. After stirring at 0° C. for 30 min, this solution was added dropwise to a pre-cooled (0° C.) solution of 1-(iodomethyl)-2-methylbenzene (7.0 g, 30.0 mmol) in DMF (75 mL) over 30 min. The reaction was stirred at 0° C. for an additional 20 min and then poured into a solution of aq. NH4Cl (300 mL) and diethyl ether (300 mL). The layers were separated and the aqueous layer was extracted with Et2O (2×300 mL). The organic extracts were washed with H2O, aq. NaHSO3, dried over Mg2SO4, filtered, and concentrated. The oil was triturated with isopropanol (1 mL) and diethyl ether (75 mL) and the solid filtered to give the titled compound (5.4 g., 76%) as a white solid. LC-MS (ES) m/e 354.5 (M+H)+.

Workup

  1. additionthis solution was added dropwise to
  2. stirringThe reaction was stirred at 0° C. for an additional 20 min
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with Et2O (2×300 mL)
  5. washThe organic extracts were washed with H2O, aq. NaHSO3
  6. dry with materialdried over Mg2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe oil was triturated with isopropanol (1 mL) and diethyl ether (75 mL)
  10. filtrationthe solid filtered

Sources & evidence

ORD record
ord-96438b3521a041e4b240be93ba3f0b29
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07816395B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes