HCID 2574890, compound → HCID 22010586, compound

HRID 323172Notes

Reaction equation

HRID 323172 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:36]=[CH:35][C:20]([C:21]([N:23]([CH3:34])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31]C=O)=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[CH3:37][N:38]1[CH2:43][CH2:42][N:41]([C:44]([CH2:46][NH:47][CH3:48])=[O:45])[CH2:40][CH2:39]1.[C:49]([BH3-])#N.[Na+]>CO.C(O)(=O)C.C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([N:23]([CH3:34])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:48][N:47]([CH3:49])[CH2:46][C:44]([N:41]4[CH2:40][CH2:39][N:38]([CH3:37])[CH2:43][CH2:42]4)=[O:45])=[O:22])=[CH:35][CH:36]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 2574890HCID 2574890, compoundHCID 5003444Sodium cyanoborohydrideHCID 22010728HCID 22010728, compound

Product 1

HCID 22010586HCID 22010586, compoundYield 58.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(formylmethoxy)phenyl]benzamide (400 mg) and 4-methyl-1-(N-methylamino)methylcarbonylpiperazine (143 mg) in a mixture of methanol (15 ml) and acetic acid (0.5 ml) was added sodium cyanoborohydride (52.4 mg) and the mixture was stirred at ambient temperature for 4 hours. The solution was diluted with ethyl acetate (30 ml) and washed successively with saturated aqueous sodium hydrogen carbonate, water and brine. The organic solution was dried over magnesium sulfate and the solvent was evaporated in vacuo. The residue was purified by silica gel column (chloroform:methanol:conc. ammonia=10:1:0.1) to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-[2-[N-methyl-N-(4-methylpiperazin-1-yl)carbonylmethylamino]ethoxy]phenyl]benzamide (310 mg) as a colorless amorphous.

Workup

  1. washwashed successively with saturated aqueous sodium hydrogen carbonate, water and brine
  2. dry with materialThe organic solution was dried over magnesium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by silica gel column (chloroform:methanol:conc. ammonia=10:1:0.1)

Sources & evidence

ORD record
ord-0d9bdcec637548ee873068e0cbfeb5d3
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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