Water → HCID 59494301, compound

HRID 872037Notes

Reaction equation

HRID 872037 reaction equation
N1C=CC=CC=1.Cl[C:8]([O:10][CH3:11])=[O:9].[NH2:12][CH2:13][CH2:14][N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH2:24][N:25]([CH:33]3[CH2:35][CH2:34]3)[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:22]=2)[C:17]([Cl:36])=[CH:16]1.O>C(Cl)(Cl)Cl>[CH3:11][O:10][C:8](=[O:9])[NH:12][CH2:13][CH2:14][N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH2:24][N:25]([C:26]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:32])[CH:33]3[CH2:34][CH2:35]3)[CH:22]=2)[C:17]([Cl:36])=[CH:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6586Methyl chloroformateHCID 59494650HCID 59494650, compound

Product 1

HCID 59494301HCID 59494301, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Pyridine (80 μL) and methyl chloroformate (38 μL) were added to a solution of tert-butyl {[1-(2-aminoethyl)-3-chloro-1H-indol-6-yl]methyl}cyclopropylcarbamate (120 mg) in chloroform (4.0 ml) under ice-cooling and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine successively, dried over sodium sulfate and concentrated in vacuo. The resulted residue was purified with a silica gel column chromatography (eluting solvent: chloroform/methanol=100/1 to 20/1) to give methyl[2-(6-{[(tert-butoxycarbonyl)(cyclopropyl)amino]methyl}-3-chloro-1H-indol-1-yl)ethyl]carbamate (106 mg) as a pale yellow oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine successively
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulted residue was purified with a silica gel column chromatography (eluting solvent: chloroform/methanol=100/1 to 20/1)

Sources & evidence

ORD record
ord-60ff5ba9f0414f45b3ba13546b667d27
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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