Sodium hydride → HCID 86757747, compound

HRID 1251091Notes

Reaction equation

HRID 1251091 reaction equation
[H-].[Na+].Br[CH2:4][C:5]([NH2:7])=[O:6].[F:8][C:9]1([F:45])[CH2:10][CH2:11][N:12]([C:31]([C:33]2[S:37][C:36]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[N:35][C:34]=2[CH3:44])=[O:32])[C:13]2[CH:30]=[CH:29][CH:28]=[CH:27][C:14]=2/[C:15]/1=[CH:16]/[C:17]([N:19]1[CH2:24][CH2:23][C:22](=[N:25][OH:26])[CH2:21][CH2:20]1)=[O:18]>O1CCCC1.C(OCC)(=O)C>[F:45][C:9]1([F:8])[CH2:10][CH2:11][N:12]([C:31]([C:33]2[S:37][C:36]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)=[N:35][C:34]=2[CH3:44])=[O:32])[C:13]2[CH:30]=[CH:29][CH:28]=[CH:27][C:14]=2/[C:15]/1=[CH:16]/[C:17]([N:19]1[CH2:20][CH2:21][C:22](=[N:25][O:26][CH2:4][C:5]([NH2:7])=[O:6])[CH2:23][CH2:24]1)=[O:18]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 696322-BromoacetamideHCID 86757743HCID 86757743, compound

Product 1

HCID 86757747HCID 86757747, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (47 mg) and 58 mg of bromoacetamide were added to a solution of 150 mg of (Z)-4,4-difluoro-5-{2-[4-(hydroxyimino)piperidino]-2-oxoethylidene}-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepine in 10 ml of tetrahydrofuran, and the mixture was stirred at 0° C. for three hours. The reaction solution was diluted with ethyl acetate and washed with a saturated aqueous solution of NaCl and dried over magnesium sulfate, and the solvent was evaporated therefrom. The residue was purified by silica gel column chromatography (eluting with chloroform-methanol). The resulting residue was crystallized from diethyl ether to give 110 mg of (Z)-[(1-{[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]acetyl}piperidin-4-ylidene)aminoxy]acetamide as a pale yellow powder.

Workup

  1. washwashed with a saturated aqueous solution of NaCl
  2. dry with materialdried over magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel column chromatography (eluting with chloroform-methanol)
  5. customThe resulting residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-b1c70b29fb9e4e8d886bb9235faaa5d7
Source dataset
uspto-grants-2002_01
Patent number
US06340678B1

Reaction notes

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