Acetone → HCID 178440170, compound

HRID 248630Notes

Reaction equation

HRID 248630 reaction equation
[C:1]([C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[NH:25][N:24]=[N:23][N:22]=3)=[CH:11][CH:10]=2)[C:6]([CH2:26][CH2:27][CH3:28])=[N:5][C:4]=1[N:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])#[N:2].[BH4-].[Na+].CC(C)=O>C(O)C>[C:1]([C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[NH:22][N:23]=[N:24][N:25]=3)=[CH:11][CH:10]=2)[C:6]([CH2:26][CH2:27][CH3:28])=[N:5][C:4]=1[N:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[CH:34]([OH:39])[C:35]([F:38])([F:36])[F:37])#[N:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 178440169HCID 178440169, compound

Product 1

HCID 178440170HCID 178440170, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-cyano-4-[2-(1-oxo-2,2,2-trifluoroethyl)-1H-pyrrol-1-yl]-2 propyl-1-[(2'-(1H-tetrazol-5-yl)biphen-4-yl)methyl]-1H-imidazole (Example 27, 300 mg) in ethanol (5 mL) was chilled to 10° C. and treated with NaBH4 (30 mg). There was a period of rapid gas evolution then the reaction was stirred for 1 hour. Acetone (0.1 mL) was added and the reaction was stirred 10 minutes longer before partitioning between ethyl acetate and 10% citric acid (aq). The organic layer was washed with saturated aqueous NaCl, dried over MgSO4 and evaporated. Flash chromatography on silica gel, eluting with CHCl3CH3OH--CH3CN (90:5:5) gives the title compound as a foam upon evaporation of solvents. The foam was triturated with hexane diisopropyl ether (3:1) to give a colorless powder. MS (FAB, thioglycerol) 533 (m+1).

Workup

  1. waitThere was a period of rapid gas evolution
  2. stirringthe reaction was stirred 10 minutes longer
  3. custombefore partitioning between ethyl acetate and 10% citric acid (aq)
  4. washThe organic layer was washed with saturated aqueous NaCl
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. washFlash chromatography on silica gel, eluting with CHCl3CH3OH

Sources & evidence

ORD record
ord-880b7e5d8f3a43d4b5df11feda4c85f5
Source dataset
uspto-grants-1993_05
Patent number
US05210211

Reaction notes

Loading…