Sodium hydride → 1-({4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)-3,3-diphenylpyrrolidin-2-one

HRID 1667199

반응식

HRID 1667199 반응식
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH2:10][NH:9][C:8]2=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:22][C:23]1[S:27][C:26]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)=[N:25][C:24]=1[CH3:38]>CN(C)C=O>[CH3:38][C:24]1[N:25]=[C:26]([C:28]2[CH:29]=[CH:30][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:32][CH:33]=2)[S:27][C:23]=1[CH2:22][N:9]1[CH2:10][CH2:11][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:8]1=[O:12]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 2382533,3-Diphenyl-2-pyrrolidinoneHCID 27946295-(Bromomethyl)-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole

생성물 1

HCID 673577121-({4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)-3,3-diphenylpyrrolidin-2-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of 3,3-diphenylpyrrolidin-2-one (Example 1A) (0.062 g, 0.262 mmol) in N,N-dimethylformamide (2 mL) was added 60% sodium hydride dispersion in oil (0.013 g, 0.314 mmol). The mixture was stirred at room temperature for 1 hour. Then a solution of 5-(bromomethyl)-4-methyl-2-(4-(trifluoromethyl)phenyl)thiazole (CAS 439134-78-8) (0.088 g, 0.262 mmol) in N,N-dimethylformamide (1 mL) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated and the residue was partitioned between H2O and dichloromethane. The organic layer was separated, dried over MgSO4 and concentrated. The obtained residue was purified by silica gel chromatography eluting with 2-5% methanol/dichloromethane to yield the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.95-8.00 (m, 2H), 7.65-7.70 (m, 2H), 7.17-7.37 (m, 10H), 4.72 (s, 2H), 3.35 (t, J=6.4 Hz, 2H), 2.76 (t, J=6.3 Hz, 2H), 2.47 (s, 3H); MS (ESI+) m/z 493 (M+H)+.

후처리

  1. stirringthe mixture was stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between H2O and dichloromethane
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe obtained residue was purified by silica gel chromatography
  8. washeluting with 2-5% methanol/dichloromethane

출처 및 근거

ORD 기록
ord-2d1f68eb38ba429f8a4192d98f758751
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044069B2

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