Dimethylformamide → HCID 67333300, compound

HRID 1942539Notes

Reaction equation

[CH:1]([N:4]([C:18]([C:20]1[CH:28]=[C:27]2[C:23]([C:24]([CH3:37])([CH3:36])[C:25](=[O:35])[N:26]2[CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH3:34])=[CH:22][CH:21]=1)=[O:19])[C@@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1)([CH3:3])[CH3:2].C1C(=O)N([Cl:45])C(=O)C1.CN(C=O)C>O>[Cl:45][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][C:20]=1[C:18]([N:4]([CH:1]([CH3:3])[CH3:2])[C@@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1)=[O:19])[N:26]([CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH3:34])[C:25](=[O:35])[C:24]2([CH3:36])[CH3:37]

Participants

Conditions

Temperature: 65 °C

Procedure

To tert-butyl (3R)-3-(isopropyl{[1-(4-methoxybutyl)-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-6-yl]carbonyl}amino)piperidine-1-carboxylate (220 mg) were added NCS (86 mg) and DMF (5 ml), and the mixture was stirred at 65° C. for one hour. After the reaction was complete, water was added to the reaction solution, and the mixture was extracted with ethyl acetate solution. This ethyl acetate was washed with water and an aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the title compound (200 mg) as a colorless liquid.

Workup

extractionthe mixture was extracted with ethyl acetate solution
washThis ethyl acetate was washed with water
dry with materialan aqueous sodium chloride solution, dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record: ord-d8510fd081b04c71aa8a01643f13b72c
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389511B2

Reaction notes

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