Formaldehyde → HCID 18791404, compound

HRID 1005590Notes

Reaction equation

HRID 1005590 reaction equation
N[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:45]=[CH:44][CH:43]=[CH:42][C:7]=1[C:8]([NH:10][C:11]1[CH:41]=[CH:40][C:14]([C:15]([N:17]([CH3:39])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([N:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]2)=[O:31])=[O:16])=[CH:13][CH:12]=1)=[O:9].[CH2:46]=O.[C:48]([BH3-])#[N:49].[Na+]>CO.C(O)(=O)C.C(Cl)(Cl)Cl>[CH3:46][N:49]([CH3:48])[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:45]=[CH:44][CH:43]=[CH:42][C:7]=1[C:8]([NH:10][C:11]1[CH:41]=[CH:40][C:14]([C:15]([N:17]([CH3:39])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([N:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]2)=[O:31])=[O:16])=[CH:13][CH:12]=1)=[O:9]

Participants

7

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 11104071HCID 11104071, compound

Product 1

HCID 18791404HCID 18791404, compoundYield 93.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a mixture of 4-[2-[(3-aminoprop-1-yl)oxy]benzoyl]amino-N-methyl-N-[2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (220 mg) and 37% aqueous formaldehyde (290 mg) in a mixture of methanol (10 ml) and acetic acid (0.2 ml) was added sodium cyanoborohydride (44.8 mg) and the mixture was stirred at ambient temperature for 4 hours. The reaction mixture was diluted with chloroform (20 ml) and the solution was washed successively with saturated aqueous sodium hydrogen carbonate solution (20 ml), water (10 ml) and brine (10 ml). The organic phase was dried over magnesium sulfate and the solvent was evaporated to give 4-[2-[(3-dimethylaminoprop-1-yl)oxy]benzoyl]amino-N-methyl-N-[2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (215 mg) as a colorless amorphous.

Workup

  1. washthe solution was washed successively with saturated aqueous sodium hydrogen carbonate solution (20 ml), water (10 ml) and brine (10 ml)
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0c9a9569f3db465dbbee4f1bbc5eecb4
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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