2-Methyltetrahydrofuran → tert-Butyl (4-Cyano-2-(methylsulfonyl)phenyl)(5-oxo-2-(2-(trifluoromethyl)pyridin-4-ylamino)cyclopent-1-enyl)methylcarbamate

HRID 927204Notes

Reaction equation

HRID 927204 reaction equation
[H-].[Na+].[F:3][C:4]([F:19])([F:18])[C:5]1[CH:10]=[C:9]([NH:11][C:12]2[CH2:16][CH2:15][C:14](=[O:17])[CH:13]=2)[CH:8]=[CH:7][N:6]=1.CC1CCCO1.[C:26]([C:28]1[CH:33]=[CH:32][C:31]([N:34]([CH2:42]S(C2C=CC=CC=2)(=O)=O)[C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[C:30]([S:52]([CH3:55])(=[O:54])=[O:53])[CH:29]=1)#[N:27]>C(OCC)(=O)C.O>[C:26]([C:28]1[CH:33]=[CH:32][C:31]([N:34]([CH2:42][C:13]2[C:14](=[O:17])[CH2:15][CH2:16][C:12]=2[NH:11][C:9]2[CH:8]=[CH:7][N:6]=[C:5]([C:4]([F:3])([F:18])[F:19])[CH:10]=2)[C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[C:30]([S:52]([CH3:55])(=[O:53])=[O:54])[CH:29]=1)#[N:27]

Participants

7

Reactant 4

HCID 73012-MethyltetrahydrofuranHCID 24758Sodium hydrideHCID 86732345tert-Butyl (4-Cyano-2-(methylsulfonyl)phenyl)(phenylsulfonyl)methylcarbamate2×HCID 903110023-(2-(Trifluoromethyl)pyridin-4-ylamino)cyclopent-2-enone2×

Product 1

HCID 131735052tert-Butyl (4-Cyano-2-(methylsulfonyl)phenyl)(5-oxo-2-(2-(trifluoromethyl)pyridin-4-ylamino)cyclopent-1-enyl)methylcarbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% in mineral oil, 515 mg, 12.9 mmol) is added in portions to a mixture of 3-(2-(trifluoromethyl)pyridin-4-ylamino)cyclopent-2-enone (intermediate 17, 2.60 g, 10.7 mmol) and 2-methyltetrahydrofuran (40 mL). After 10 min tert-butyl (4-cyano-2-(methylsulfonyl)phenyl)(phenylsulfonyl)methylcarbamate (intermediate 15, 4.83 g, 10.7 mmol) is added, and the mixture is stirred at room temperature for 30 min Water and ethyl acetate are added, and the phases are separated. The organic phases is washed twice with water and concentrated under reduced pressure. Yield: 6.20 g; ESI mass spectrum [M+H]+=551; Retention time HPLC: 1.12 min (Z018_S04).

Workup

  1. additionare added
  2. customthe phases are separated
  3. washThe organic phases is washed twice with water
  4. concentrationconcentrated under reduced pressure
  5. custom1.12 min (Z018_S04)

Sources & evidence

ORD record
ord-25765cc5e1c4414596da5e9f7c804fe7
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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