Triethylamine → HCID 86757743, compound

HRID 1251084Notes

Reaction equation

HRID 1251084 reaction equation
[F:1][C:2]1([F:37])[CH2:3][CH2:4][N:5]([C:23]([C:25]2[S:29][C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:27][C:26]=2[CH3:36])=[O:24])[C:6]2[CH:22]=[CH:21][CH:20]=[CH:19][C:7]=2/[C:8]/1=[CH:9]/[C:10]([N:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1)=[O:11].Cl.[NH2:39][OH:40].C(N(CC)CC)C>ClCCl.CO>[F:37][C:2]1([F:1])[CH2:3][CH2:4][N:5]([C:23]([C:25]2[S:29][C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:27][C:26]=2[CH3:36])=[O:24])[C:6]2[CH:22]=[CH:21][CH:20]=[CH:19][C:7]=2/[C:8]/1=[CH:9]/[C:10]([N:12]1[CH2:17][CH2:16][C:15](=[N:39][OH:40])[CH2:14][CH2:13]1)=[O:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 70161361HCID 70161361, compound

Product 1

HCID 86757743HCID 86757743, compoundYield 29.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 200 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-one in a mixture of 6 ml of dichloromethane and 3 ml of methanol were added 29 mg of hydroxylamine monohydrochloride and 59 μl of triethylamine, followed by stirring at room temperature for 22 hours. After evaporating the solvent, the residue was purified by silica gel column chromatography (eluting with chloroform-methanol), followed by crystallizing from diethyl ether to give 61 mg of (Z)-4,4-difluoro-5-{2-[4-(hydroxyimino)piperidino]-2-oxo-ethylidene}-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepine as a colorless powder.

Workup

  1. customAfter evaporating the solvent
  2. customthe residue was purified by silica gel column chromatography (eluting with chloroform-methanol)
  3. customby crystallizing from diethyl ether

Sources & evidence

ORD record
ord-596513dc5e414ec7a47505527fd2f0fe
Source dataset
uspto-grants-2002_01
Patent number
US06340678B1

Reaction notes

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