2-Methyltetrahydrofuran → HCID 86732346, compound

HRID 517226Notes

Reaction equation

HRID 517226 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:19]S(C2C=CC=CC=2)(=O)=O)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[C:7]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:6]=1)#[N:4].CC1CCCO1.[F:39][C:40]([F:56])([F:55])[C:41]1[CH:46]=[C:45]([NH:47][C:48]2[CH2:53][CH2:52][CH2:51][C:50](=[O:54])[CH:49]=2)[CH:44]=[CH:43][N:42]=1>O>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:19][C:49]2[C:50](=[O:54])[CH2:51][CH2:52][CH2:53][C:48]=2[NH:47][C:45]2[CH:44]=[CH:43][N:42]=[C:41]([C:40]([F:39])([F:55])[F:56])[CH:46]=2)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[C:7]([S:29]([CH3:32])(=[O:30])=[O:31])[CH:6]=1)#[N:4]

Participants

6

Reactant 4

HCID 73012-MethyltetrahydrofuranHCID 24758Sodium hydrideHCID 86732345tert-Butyl (4-Cyano-2-(methylsulfonyl)phenyl)(phenylsulfonyl)methylcarbamateHCID 86732347HCID 86732347, compound2×

Product 1

HCID 86732346HCID 86732346, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% in mineral oil, 153 mg, 3.84 mmol) is added in portions to a mixture of tert-butyl (4-cyano-2-(methylsulfonyl)phenyl)(phenylsulfonyl)methylcarbamate (step 1, 1.60 g, 3.20 mmol based on 90% purity) and 2-methyltetrahydrofuran (15 mL), and the mixture is stirred at room temperature for 20 min. 3-(2-(Trifluoromethyl)pyridin-4-yl-amino)cyclohex-2-enone (intermediate 55, 940 mg, 3.70 mmol) is added, and the mixture is stirred for 2 h. Water is added, and the phases are separated. The organic layer is washed with water and concentrated under reduced pressure. The residue is purified by flash chromatography on silica (gradient dichloromethane/methanol 99:1 to 97/3). Yield: 2.10 g; ESI mass spectrum [M+H]+=565; Retention time HPLC: 0.67 min (X012_S02).

Workup

  1. stirringthe mixture is stirred for 2 h
  2. customthe phases are separated
  3. washThe organic layer is washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by flash chromatography on silica (gradient dichloromethane/methanol 99:1 to 97/3)
  6. custom0.67 min (X012_S02)

Sources & evidence

ORD record
ord-fd6f169116504da18e18a35d8072b3c4
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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