Hydrochloric Acid → HCID 86584134, compound

HRID 1596373Notes

Reaction equation

HRID 1596373 reaction equation
[CH:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:10]([CH2:12][N:13]1[C:19]3[C:20]([CH3:24])=[CH:21][CH:22]=[CH:23][C:18]=3[C:17]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])=[N:16][CH:15]([NH:32][C:33]([NH:35][C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([C:42](=O)[CH3:43])[CH:37]=3)=[O:34])[C:14]1=[O:45])=[O:11])[CH2:2]2.Cl.[NH2:47][OH:48].C(N(CC)CC)C.Cl>O1CCCC1.C(OCC)(=O)C>[CH:5]12[CH2:6][CH2:7][CH:1]([CH2:9][CH2:8]1)[CH2:2][N:3]([C:10]([CH2:12][N:13]1[C:19]3[C:20]([CH3:24])=[CH:21][CH:22]=[CH:23][C:18]=3[C:17]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])=[N:16][CH:15]([NH:32][C:33]([NH:35][C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([C:42](=[N:47][OH:48])[CH3:43])[CH:37]=3)=[O:34])[C:14]1=[O:45])=[O:11])[CH2:4]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 44293998HCID 44293998, compound

Product 1

HCID 86584134HCID 86584134, compoundYield 105.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-[(3RS)-1-(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl-2,3-dihydro-9-methyl-5-(2-fluorophenyl)-2-oxo-1H-1,4-benzodiazepin-3-yl]-N′-(3-acetylphenyl)urea (217 mg) and hydroxylamine-hydrochloride (124 mg), triethylamine (180 mg) in tetrahydrofuran (4 ml) was stirred at room temperature overnight. Ethyl acetate and 1N aqueous hydrochloric acid solution were added the reaction mixture. The separated organic layer was washed with 1N aqueous hydrochloric acid twice, saturated aqueous sodium bicarbonate and brine successively and then dried over magnesium sulfate. The solvent was evaporated in vacuo to afford N-[(3RS)-1-(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl-2,3-dihydro-9-methyl-5-(2-fluorophenyl)-2-oxo-1H-1,4-benzodiazepin-3-yl]-N′-[3-(1-hydroxyiminoethyl)phenyl]urea (235.0 mg) as a crystalline powder.

Workup

  1. washThe separated organic layer was washed with 1N aqueous hydrochloric acid twice
  2. dry with materialsaturated aqueous sodium bicarbonate and brine successively and then dried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-c6d8300ff98a49a2b10d7f6c701272ec
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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