HCID 70247567, compound → HCID 22004135, compound

HRID 324281Notes

Reaction equation

HRID 324281 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[C:18]([C:19](O)=[O:20])=[CH:17][C:7]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=1>C1COCC1>[ClH:1].[OH:20][CH2:19][C:18]1[C:4]([O:3][CH3:2])=[CH:5][C:6]2[N:10]=[CH:9][N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7]=2[CH:17]=1

Participants

3

Reactant 1

HCID 70247567HCID 70247567, compound

Product 1

HCID 22004135HCID 22004135, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-methyl sulfide complex (1.11 mL of 10.0N, 0.011 mol) was added dropwise at room temperature under nitrogen to a stirred sclution of 5-methoxy-1-phenylbenzimidazole-6-carboxylic acid hydrochloride(1.00 g, 3.73 mmol) in THF (60 mL). After stirring at this temperature for 3 hours, the excess of reagent was destroyed by careful addition of MeOH, followed by water, and the solution was acidified with 3N HCl and stirred at room temperature for a further 30 minutes. The aqueous solution was washed with EtOAc, then basified with conc. NH3 solution, extracted with EtOAc, and the organic portion worked up to give an oily solid which was chromatographed on silica gel. EtOAc eluted foreruns, while MeOH/EtOAc (1:15) eluted the alcohol Example 53 (0.77 g, 81%). HCl salt: mp (MeOH/Et2O) 260° C. (dec.).

Workup

  1. customthe excess of reagent was destroyed by careful addition of MeOH
  2. stirringstirred at room temperature for a further 30 minutes
  3. washThe aqueous solution was washed with EtOAc
  4. extractionextracted with EtOAc
  5. customto give an oily solid which
  6. customwas chromatographed on silica gel
  7. washEtOAc eluted foreruns, while MeOH/EtOAc (1:15) eluted the alcohol Example 53 (0.77 g, 81%)

Sources & evidence

ORD record
ord-5a10b2b89e394fd8b9df9affb6603cf4
Source dataset
uspto-grants-2001_04
Patent number
US06218388B1

Reaction notes

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