Formaldehyde → HCID 86757596, compound

HRID 429691Notes

Reaction equation

HRID 429691 reaction equation
N[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[N:14]([CH3:38])[C:15](=[O:37])[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:30]3[N:29]=[C:28]([CH3:31])[NH:27][C:26]=3[CH:25]=[CH:24][CH:23]=2)=[C:18]([O:32][CH3:33])[C:17]=1[N:34]=[C:35]=[O:36].[CH2:39]=O.[C:41]([BH3-])#[N:42].[Na+]>CO.C(Cl)(Cl)Cl>[CH3:39][N:42]([CH3:41])[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[N:14]([CH3:38])[C:15](=[O:37])[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:30]3[N:29]=[C:28]([CH3:31])[NH:27][C:26]=3[CH:25]=[CH:24][CH:23]=2)=[C:18]([O:32][CH3:33])[C:17]=1[N:34]=[C:35]=[O:36]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86757597HCID 86757597, compound

Product 1

HCID 86757596HCID 86757596, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of N-[2-(4-aminobut-1-yloxy)-4-methylphenyl]-3-methoxy-N-methyl-4-(2-methyl-1H-benzimidazol-4-yl)-carbonylaminobenzamide (150 mg), 37% formaldehyde solution (43.7 mg) and sodium cyanoborohydride (18.3 mg) in methanol (10 ml) was stirred at ambient temperature for 6 hours. The mixture was diluted with chloroform and the solution was washed with saturated aqueous sodium hydrogen carbonate and brine. The organic phase was dried over magnesium sulfate and the solvent was evaporated in vacuo. The crude product was purified by silica gel column (5% methanol in chloroform) to give N-[2-(4-dimethylaminobut-1-yloxy)-4-methylphenyl]-3-methoxy-N-methyl-4-(2-methyl-1H-benzimidazol-4-yl)-carbonylaminobenzamide (142 mg).

Workup

  1. washthe solution was washed with saturated aqueous sodium hydrogen carbonate and brine
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customThe crude product was purified by silica gel column (5% methanol in chloroform)

Sources & evidence

ORD record
ord-c9c0b0d63f6b490189d512e05145a59d
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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