Acetyl chloride → HCID 86656366, compound

HRID 1942541Notes

Reaction equation

HRID 1942541 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([N:15]([CH:29]([CH3:31])[CH3:30])[C@@H:16]3[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]3)=[O:14])[CH:11]=2)[C:6]([CH3:33])([CH3:32])[C:5]1=[O:34].C(N([CH2:40][CH3:41])CC)C.[C:42](Cl)(=[O:44])C>C1COCC1>[CH3:33][C:6]1([CH3:32])[C:7]2[C:12](=[CH:11][C:10]([C:13]([N:15]([CH:29]([CH3:30])[CH3:31])[C@@H:16]3[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:17]3)=[O:14])=[CH:9][CH:8]=2)[N:4]([CH2:3][CH2:2][NH:1][C:42](=[O:44])[CH2:40][CH3:41])[C:5]1=[O:34]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67331329HCID 67331329, compound

Product 1

HCID 86656366HCID 86656366, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To tert-butyl (3R)-3-[{[1-(2-aminoethyl)-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-6-yl]carbonyl}(isopropyl)amino]piperidine-1-carboxylate (300 mg) were added triethylamine (0.14 ml), THF (3 ml) and acetyl chloride (0.07 ml) under ice-cooling, and the mixture was stirred at room temperature for one hour. After the reaction was complete, the mixture was concentrated, and the obtained residue was purified by silica gel column chromatography (chloroform/methanol=9/1) to give the title compound (190 mg) as colorless amorphous.

Workup

  1. temperaturecooling
  2. concentrationthe mixture was concentrated
  3. customthe obtained residue was purified by silica gel column chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-bd02fc3a01424562972ddd4a76891c05
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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