Acetone → HCID 86591637, compound

HRID 1062449Notes

Reaction equation

HRID 1062449 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[NH:14][C:15]([C:17]1[N:18]=[C:19]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:35])[N:20]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH:21]=1)=[O:16])(=O)C.[BH4-].[Na+].CC(C)=O>C1COCC1.O>[Cl:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:19]1[N:20]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH:21]=[C:17]([C:15]([NH:14][C@@H:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C@@H:8]2[O:7][CH2:6][CH2:5][OH:4])=[O:16])[N:18]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 69747343HCID 69747343, compound

Product 1

HCID 86591637HCID 86591637, compoundYield 26.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{[trans-2-({[2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazol-4-yl]carbonyl}amino)cyclohexyl]oxy}-ethyl acetate (Table entry 286) (31 mg, 0.06 mmol) in THF (7 mL) and water (0.7 mL) was added NaBH4 (5 mg, 0.13 mmol) portionwise over 1 h with the temperature kept below 20° C. The mixture was stirred at rt overnight, cooled to 5° C., treated with acetone (1 mL), and then concentrated. The residue was dissolved in CH2Cl2 and washed with brine. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (2.5% methanol in EtOAc) to give the product 2-(2-chlorophenyl)-1-(4-chlorophenyl)-N-[(1R, 2S)-2-(2-hydroxyethoxy)cyclohexyl]-1H-imidazole-4-carboxamide (7.5 mg, 26% yield): LC-MS m/z (474.8 MH+), retention time 2.91 min (method 1); Rf=0.17 (EtOAc).

Workup

  1. customkept below 20° C
  2. temperaturecooled to 5° C.
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in CH2Cl2
  5. washwashed with brine
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (2.5% methanol in EtOAc)

Sources & evidence

ORD record
ord-ba80d72d81b04a47b4004e41c26c02cb
Source dataset
uspto-grants-2005_11
Patent number
US06960601B2

Reaction notes

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