Sodium hydride → HCID 86656369, compound

HRID 1942548Notes

Reaction equation

HRID 1942548 reaction equation
[OH:1][CH2:2][C:3]1([CH3:43])[C:8](=[O:9])[N:7]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[C:6]2[CH:16]=[C:17]([C:24]([N:26]([CH:40]([CH3:42])[CH3:41])[C@@H:27]3[CH2:32][CH2:31][CH2:30][N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28]3)=[O:25])[C:18]([C:20]([F:23])([F:22])[F:21])=[CH:19][C:5]=2[O:4]1.[H-].[Na+].[CH3:46][O:47][CH2:48][CH2:49]Br.[Cl-].[NH4+]>CN(C)C=O>[CH:40]([N:26]([C:24]([C:17]1[C:18]([C:20]([F:23])([F:21])[F:22])=[CH:19][C:5]2[O:4][C:3]([CH2:2][O:1][CH2:49][CH2:48][O:47][CH3:46])([CH3:43])[C:8](=[O:9])[N:7]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[C:6]=2[CH:16]=1)=[O:25])[C@@H:27]1[CH2:32][CH2:31][CH2:30][N:29]([C:33]([O:35][C:36]([CH3:37])([CH3:39])[CH3:38])=[O:34])[CH2:28]1)([CH3:41])[CH3:42]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 809722-Bromoethyl methyl etherHCID 67330888HCID 67330888, compound

Product 1

HCID 86656369HCID 86656369, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl (3R)-3-[{[2-(hydroxymethyl)-4-(4-methoxybutyl)-2-methyl-3-oxo-7-(trifluoromethyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]carbonyl}(isopropyl)amino]piperidine-1-carboxylate (230 mg) in N,N-dimethylformamide (3 ml) were added sodium hydride (50 mg, 55% by weight) and 2-bromoethyl methyl ether (0.11 ml), and the mixture was stirred at 80° C. for 3 hours. To the reaction solution was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The mixture was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (110 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe mixture was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0832e28923d54d7fa6089afbe57dc509
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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