Water → HCID 118509535, compound

HRID 1487277Notes

Reaction equation

HRID 1487277 reaction equation
F[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:16])([CH3:15])[C:7](=[O:14])[N:8]2[CH:11]([CH3:13])[CH3:12])=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].CCN(C(C)C)C(C)C.[C:29]1([C@@H:35]([NH2:37])[CH3:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.O>CN1C(=O)CCC1>[CH:11]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([N+:17]([O-:19])=[O:18])=[C:2]([NH:37][C@H:35]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH3:36])[CH:10]=2)[C:6]([CH3:16])([CH3:15])[C:7]1=[O:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 758181-Phenethylamine, (-)-HCID 81531DiisopropylethylamineHCID 118509537HCID 118509537, compound

Product 1

HCID 118509535HCID 118509535, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
50 °C

Procedure

6-Fluoro-1-isopropyl-3,3-dimethyl-5-nitro-1,3-dihydro-indol-2-one E-1.2″ (4.5 g; 16.5 mmol) is dissolved in NMP (20 ml), DIPEA (4.0 ml; 22.3 mmol) and (S)-1-Phenyl-ethylamine (2.65 ml; 20.1 mmol) is added at 20° C. The reaction mixture is stirred for 3 h at 50° C. The reaction mixture is poured into water and extracted with DCM. The combined organic layer is dried over MgSO4 and concentrated under reduced pressure. The crude compound was purified by column chromatography using silica gel (50 μM) with eluting mixture of ethyl acetate and cyclohexane.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic layer is dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude compound was purified by column chromatography
  5. washwith eluting
  6. additionmixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-a7de8c40fa864f08954d095309f0cecc
Source dataset
uspto-grants-2016_08
Patent number
US09428515B2

Reaction notes

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