2-Methyltetrahydrofuran → HCID 131735051, compound

HRID 927203Notes

Reaction equation

HRID 927203 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])=[CH:30][CH:29]=1)#[N:27]>O>[C:37]([O:36][C:35](=[O:41])[N:34]([C:31]1[CH:30]=[CH:29][C:28]([C:26]#[N:27])=[CH:33][CH:32]=1)[CH2:42][C:13]1[C:14](=[O:17])[CH2:15][CH2:16][C:12]=1[NH:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]([C:4]([F:3])([F:18])[F:19])[CH:10]=1)([CH3:40])([CH3:38])[CH3:39]

Participants

6

Reactant 4

HCID 73012-MethyltetrahydrofuranHCID 24758Sodium hydrideHCID 903110023-(2-(Trifluoromethyl)pyridin-4-ylamino)cyclopent-2-enone2×HCID 129539717Tert-butyl(4-cyanophenyl)(phenylsulfonyl)methylcarbamate

Product 1

HCID 131735051HCID 131735051, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% in mineral oil, 895 mg, 22.4 mmol) is added in portions to a mixture of 3-(2-(trifluoromethyl)pyridin-4-ylamino)cyclopent-2-enone (intermediate 17, 4.52 g, 18.7 mmol) and 2-methyltetrahydrofuran (30 mL). After 30 min tert-butyl (4-cyano-phenyl)(phenylsulfonyl)methylcarbamate (6.90 g, 18.5 mmol) is added, and mixture is stirred at room temperature for 30 min Water is added, and the phases are separated. The organic phase is dried over Na2SO4 and concentrated under reduced pressure. Yield: 9.20 g; ESI mass spectrum [M+H]+=473; Retention time HPLC: 1.09 min (Z018_504).

Workup

  1. additionis added
  2. customthe phases are separated
  3. dry with materialThe organic phase is dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. custom1.09 min (Z018_504)

Sources & evidence

ORD record
ord-79998569317144fbb002cf92b9119a60
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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