Ammonium Hydroxide → HCID 69021420, compound

HRID 860782Notes

Reaction equation

HRID 860782 reaction equation
[BH3-]C#N.[Na+].[Cl:5][C:6]1[CH:33]=[CH:32][C:9]([C:10]([C:12]2[CH:13]=[CH:14][C:15]3[N:21]([CH3:22])[C:20](=[O:23])[CH2:19][N:18]=[C:17]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=4)[C:16]=3[CH:31]=2)=[O:11])=[CH:8][CH:7]=1.[NH4+].[OH-]>C(O)(=O)C.CO>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([C:12]2[CH:13]=[CH:14][C:15]3[N:21]([CH3:22])[C:20](=[O:23])[CH2:19][NH:18][CH:17]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=4)[C:16]=3[CH:31]=2)=[O:11])=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 69020511HCID 69020511, compound

Product 1

HCID 69021420HCID 69021420, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

NaBH3CN (0.0472 mol) was added at 5° C. to a mixture of intermediate (7) (0.0236 mol) in acetic acid (50 ml) and methanol (300 ml). The mixture was stirred at 5° C. for 30 min and then stirred at room temperature for 2 hours. Ice water and then NH4OH 35% (60 ml) were added. The mixture was stirred for 2 hours. The precipitate was filtered off, washed with water and taken up in DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated, yielding 8.25 g (85%) of 7-(4-chlorobenzoyl)-5-(3-chlorophenyl)-1,3,4,5-tetrahydro-1-methyl-2H-1,4-benzodiazepin-2-one (intermediate 8), mp. 177° C.

Workup

  1. stirringstirred at room temperature for 2 hours
  2. stirringThe mixture was stirred for 2 hours
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6ef7e114a7b24f639028a52afb7359a1
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

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