Water → HCID 25212824, compound

HRID 561356

Reaction equation

HRID 561356 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([NH2:17])=[O:16])[CH:10]=2)=[CH:5][CH:4]=1)=O.[CH3:18][CH:19]1[CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21][CH2:20]1.[BH4-].[Na+].O>CO>[CH3:18][CH:19]1[CH2:24][CH2:23][CH:22]([NH:25][CH2:1][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([NH2:17])=[O:16])[CH:10]=3)=[CH:5][CH:4]=2)[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 806044-MethylcyclohexylamineHCID 4311764Sodium borohydrideHCID 593165294'-Formyl-3-biphenylcarboxamide

Product 1

HCID 25212824HCID 25212824, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4′-formylbiphenyl-3-carboxylic acid amide (700 mg, 3.1 mmol) in methanol (15 mL) was added 4 Å molecular sieves (700 mg) and 4-methylcyclohexylamine (421 mg, 3.7 mmol). The mixture was stirred for 16 h before adding sodium borohydride (588 mg, 15.5 mmol). After 1 h water (10 mL) was added, the mixture was filtered through celite and the solvent removed in vacuo. Purification of the residue by column chromatography (0.5% NH3: 6% MeOH: DCM) gave the title compound: RT=2.53 min; m/z (ES+)=323.0 [M+H]+.

Workup

  1. filtrationthe mixture was filtered through celite
  2. customthe solvent removed in vacuo
  3. customPurification of the residue by column chromatography (0.5% NH3: 6% MeOH: DCM)

Sources & evidence

ORD record
ord-fdfd0688c00c4d4cbba2615508c03b73
Source dataset
uspto-grants-2011_11
Patent number
US08063247B2

Linked notes

Loading…