Water → HCID 178423607, compound

HRID 1596370Notes

Reaction equation

HRID 1596370 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[C:18]([CH3:19])[C:13]=2[N:12]([CH2:20][C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29]C)=[O:22])[C:11](=[O:31])[CH:10]([NH:32][C:33]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([C:42]3[NH:46][N:45]=[N:44][N:43]=3)[CH:37]=2)=[O:34])[N:9]=1.B(Br)(Br)Br.C(OCC)(=O)C.O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[C:18]([CH3:19])[C:13]=2[N:12]([CH2:20][C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[OH:29])=[O:22])[C:11](=[O:31])[CH:10]([NH:32][C:33]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([C:42]3[NH:46][N:45]=[N:44][N:43]=3)[CH:37]=2)=[O:34])[N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 178489552HCID 178489552, compound

Product 1

HCID 178423607HCID 178423607, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of N-[(3RS)-2,3-dihydro-5-(2-fluorophenyl)-1-(2-methoxyphenacyl)-9-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]-N′-[3-(tetrazol-5-yl)phenyl]urea (200 mg) and 1N boron tribromide in methylene chloride (3.87 ml) was stirred at 0° C. under nitrogen stream for 4 hours and allowed to stand in a refrigerator overnight. Ethyl acetate and water were added to the reaction mixture. The separated organic layer was washed with water and brine, and then dried over magnesium sulfate. The solvent was evaporated in vacuo to afford a pale brown powder, which was washed with diisopropyl ether and collected by filtration to give N-[(3RS)-2,3-dihydro-5-(2-fluorophenyl)-1-(2-hydroxyphenacyl)-9-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]-N′-[3-(tetrazol-5-yl)phenyl]urea (202.0 mg) as a crystalline powder.

Workup

  1. customto stand in a refrigerator overnight
  2. washThe separated organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customto afford a pale brown powder, which
  6. washwas washed with diisopropyl ether
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-c0186e5d23784859b8bd9219d2099364
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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