Hydrochloric Acid → HCID 70126932, compound

HRID 1596375Notes

Reaction equation

HRID 1596375 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]([N:35]3[CH:39]=[CH:38]N=C3)=[O:34])[C:14]1=[O:40])=[O:11])[CH2:2]2.N[C:42]1[CH:43]=[C:44]([OH:48])C=C[CH:47]=1.C(N(CC)CC)C.Cl>CN(C)C=O.C(OCC)(=O)C>[CH:1]12[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9]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:39]3[CH:47]=[CH:42][CH:43]=[C:44]([OH:48])[CH:38]=3)=[O:34])[C:14]1=[O:40])=[O:11])[CH2:2]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 115683-AminophenolHCID 70126426HCID 70126426, compound

Product 1

HCID 70126932HCID 70126932, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (3RS)-1-[(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl]-2,3-dihydro-5-(2-fluorophenyl)-3-(imidazol-1-yl)carbonylamino-9-methyl-1H-1,4-benzodiazepin-2-one (250 mg), 3-aminophenol (55 mg) and triethylamine (93 mg) in N,N-dimethylformamide (1 ml) was stirred at 100° C. for 1 hour. After the reaction mixture was allowed to cool to room temperature, ethyl acetate and 1N aqueous hydrochloric acid were added thereto. The separated organic layer was washed with 1N aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate and brine successively, and then dried over magnesium sulfate. The solvent was evaporated in vacuo to give a colorless paste, which was washed with diisopropyl ether and collected by filtration 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-hydroxyphenyl)urea (184.0 mg, 68.5% yield) as a crystalline.

Workup

  1. temperatureto cool to room temperature
  2. washThe separated organic layer was washed with 1N aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate and brine successively
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customto give a colorless paste, which
  6. washwas washed with diisopropyl ether
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-ce11827f138b4fa99c94ea1fa0c79091
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

Loading…