Water → HCID 19964733, compound

HRID 232984Notes

Reaction equation

HRID 232984 reaction equation
[CH:1]1([C:4]2[N:8]([CH2:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4[C:17]([C:22]([OH:24])=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=4)=[CH:12][CH:11]=3)[C:7]3[CH:25]=[C:26]([C:30]4[N:31]=[CH:32][N:33]([CH2:35][CH2:36][O:37]C)[CH:34]=4)[CH:27]=[C:28]([CH3:29])[C:6]=3[N:5]=2)[CH2:3][CH2:2]1.B(Br)(Br)Br.O>C(Cl)Cl>[CH:1]1([C:4]2[N:8]([CH2:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4[C:17]([C:22]([OH:24])=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=4)=[CH:12][CH:11]=3)[C:7]3[CH:25]=[C:26]([C:30]4[N:31]=[CH:32][N:33]([CH2:35][CH2:36][OH:37])[CH:34]=4)[CH:27]=[C:28]([CH3:29])[C:6]=3[N:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 19964563HCID 19964563, compound

Product 1

HCID 19964733HCID 19964733, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 500 mg (1.0 mMol) of 4'-[(2-cyclopropyl-4-methyl-6-(1-(2-methoxyethyl)-imidazol-4-yl)-benzimidazol-1-yl)-methyl]-biphenyl-2-carboxylic acid and 1.5 g (6.0 mMol) of boron tribromide in 50 ml of methylene chloride is stirred for 16 hours at ambient temperature, then mixed with about 30 ml of water and stirred vigorously for another 10 minutes. This mixture is evaporated to dryness and the residue is refluxed in about 40 ml of ethanol for 10 minutes. The mixture is evaporated to dryness once more, the residue is dissolved in about 30 ml of 2N ammonia solution and this solution is adjusted to pH 5-6 with 2N acetic acid. The crude product precipitated is suction filtered and purified by column chromatography (80 g silica gel; eluant:methylene chloride/methanol=4:1).

Workup

  1. customThis mixture is evaporated to dryness
  2. temperaturethe residue is refluxed in about 40 ml of ethanol for 10 minutes
  3. customThe mixture is evaporated to dryness once more
  4. dissolutionthe residue is dissolved in about 30 ml of 2N ammonia solution
  5. customThe crude product precipitated
  6. filtrationfiltered
  7. custompurified by column chromatography (80 g silica gel; eluant:methylene chloride/methanol=4:1)

Sources & evidence

ORD record
ord-13fb5bb3fee94d7a879c1ded305f201b
Source dataset
uspto-grants-1997_01
Patent number
US05591762

Reaction notes

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