Methanol → HCID 178428166, compound

HRID 1720292Notes

Reaction equation

HRID 1720292 reaction equation
ClCCl.CO[C:6]1[N:16]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[NH:34][N:33]=[N:32][N:31]=3)=[CH:20][CH:19]=2)[C:9]2=[N:10][C:11](C)=[CH:12][C:13]([CH3:14])=[C:8]2[N:7]=1.B(Br)(Br)Br.[CH3:39][OH:40]>>[OH:40][CH2:39][C:6]1[N:16]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[NH:34][N:33]=[N:32][N:31]=3)=[CH:20][CH:19]=2)[C:9]2=[N:10][CH:11]=[CH:12][C:13]([CH3:14])=[C:8]2[N:7]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 6344Dichloromethane2×HCID 25134Boron tribromideHCID 178493959HCID 178493959, compound

Product 1

HCID 178428166HCID 178428166, compound

Procedure

30 ml of a dichloromethane solution of 410 mg (1 mmol) of 2-methoxy-methyl-7-methyl-3[(2'-(1H-tetrazol-5-yl)-biphenyl-4-yl)-methyl]-3H-imidazo[4.5-b]pyridine was stirred, cooled with ice. During this step, 10 ml (10 mmol) of dichloromethane solution of 1M boron tribromide was added little by little thereto dropwise. The mixture was further agitated at a room temperature for 12 hours. The reaction product mixture was cooled, while stirred. During this step, methanol was added little by little. The solvent was distilled out at a reduced pressure. The residue was mixed with water, neutralized with sodium bicarbonate, adjusted to a weak acidity with acetic acid and decanted to remove the water. The residue was mixed with methanol. The solvent was distilled out at a reduced pressure. The residue was treated with isopropylether for re-crystallization to obtain 330 mg of the intended compound.

Workup

  1. temperaturecooled with ice
  2. temperatureThe reaction product mixture was cooled
  3. stirringwhile stirred
  4. distillationThe solvent was distilled out at a reduced pressure
  5. additionThe residue was mixed with water
  6. customdecanted
  7. customto remove the water
  8. additionThe residue was mixed with methanol
  9. distillationThe solvent was distilled out at a reduced pressure
  10. additionThe residue was treated with isopropylether for re-crystallization

Sources & evidence

ORD record
ord-0b76ace089284caa9336f10a12a72502
Source dataset
uspto-grants-1996_04
Patent number
US05506238

Reaction notes

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