Dimethylcarbamoyl Chloride → 4-(2-chloro-5-fluorophenyl)-N,N-dimethyl-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxamide

HRID 2054742Notes

Reaction equation

HRID 2054742 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]([CH3:13])[C:10](Cl)=[O:11].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[C:22]1[CH2:26][NH:25][CH:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:23]=1>ClCCl>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[C:22]1[CH2:26][N:25]([C:10]([N:9]([CH3:13])[CH3:8])=[O:11])[CH:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:23]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 596566114-(2-chloro-5-fluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole

Product 1

HCID 596566174-(2-chloro-5-fluorophenyl)-N,N-dimethyl-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.600 mL, 4.28 mmol, 5.00 equiv) and dimethylcarbamoyl chloride (0.080 mL, 0.86 mmol, 1.00 equiv) were added to a solution of 4-(2-chloro-5-fluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole (1-5, TFA salt, 0.856 mmol, 1 equiv) in dichloromethane (50 mL) at 23° C., and the resulting mixture was stirred for 2 h, then concentrated. The residue was partitioned between saturated aqueous sodium bicarbonate solution (75 mL) and ethyl acetate (100 mL). The organic layer was dried over sodium sulfate and concentrated. The residue was suspended in ethyl ether (2 mL) and the precipitate filtered to provide 4-(2-chloro-5-fluorophenyl)-N,N-dimethyl-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxamide (1-6) as an off-white solid. 1H NMR (500 MHz, CDCl3) δ 7.40-7.30 (m, 5H), 7.26 (m, 1H), 7.03 (dd, 1H, J=9.0,2.9 Hz), 6.97.(m, 1H), 6.24 (m, 1H), 6.15 (m, 1H), 4.86 (ddd, 1H, J=13.9, 5.6, 2.2 Hz), 4.49 (dt, 1H, J=13.9, 2.0 Hz), 2.86 (s, 6H). LRMS m/z (M+H) 345.0 found, 345.1 required.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between saturated aqueous sodium bicarbonate solution (75 mL) and ethyl acetate (100 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. filtrationthe precipitate filtered

Sources & evidence

ORD record
ord-4002f811c02843d89fba900f6fc0b066
Source dataset
uspto-grants-2008_02
Patent number
US07329762B2

Reaction notes

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