Formaldehyde → HCID 18354871, compound

HRID 1533816Notes

Reaction equation

HRID 1533816 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]([NH:22][C:23]([C:25]2[C:33]3[N:32]=[C:31]([CH3:34])[NH:30][C:29]=3[CH:28]=[CH:27][CH:26]=2)=[O:24])=[C:18]([O:35][CH3:36])[CH:17]=1.[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]([NH:22][C:23]([C:25]2[C:33]3[N:32]=[C:31]([CH3:34])[NH:30][C:29]=3[CH:28]=[CH:27][CH:26]=2)=[O:24])=[C:18]([O:35][CH3:36])[CH:17]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 18354848HCID 18354848, compound

Product 1

HCID 18354871HCID 18354871, compoundYield 89.8%

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-c2f53fc9c42c4c7cac113417294edbdb
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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