Ammonium Chloride → HCID 58012041, compound

HRID 660957Notes

Reaction equation

HRID 660957 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14](=[O:17])[CH2:15][CH3:16])[C:11](=[O:18])[N:10]([CH2:19][C:20]([NH:22][C:23]([CH3:35])([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=3)[CH3:24])=[O:21])[N:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH:14]([OH:17])[CH2:15][CH3:16])[C:11](=[O:18])[N:10]([CH2:19][C:20]([NH:22][C:23]([CH3:24])([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:32])([F:33])[F:34])[CH:26]=3)[CH3:35])=[O:21])[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 58011679HCID 58011679, compound

Product 1

HCID 58012041HCID 58012041, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

62 mg (0.12 mmol) of 2-[3-(4-chlorophenyl)-5-oxo-4-(2-oxobutyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-{1-methyl-1-[3-(trifluoromethyl)phenyl]ethyl}-acetamide from Example 443 are dissolved in 2 ml of methanol and treated at RT with 4.7 mg (0.12 mmol) of sodium borohydride. This is stirred for 1 hr at RT. It is then treated with saturated ammonium chloride solution and extracted with 10 ml of ethyl acetate. The organic phase is dried over sodium sulphate, filtered and concentrated. 57 mg (92% of theory) of the target compound are thus obtained.

Workup

  1. extractionextracted with 10 ml of ethyl acetate
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custom57 mg (92% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-7581745dc4384187bc74e79cb847480e
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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