HCID 18791255, compound → N-Methylbenzamide

HRID 1005600Notes

Reaction equation

HRID 1005600 reaction equation
C(OC(NCCCO[C:13]1[CH:46]=[CH:45][CH:44]=[CH:43][C:14]=1[C:15]([NH:17][C:18]1C=CC(C(N(C2C=CC(C)=CC=2OCCCCN)C)=O)=CC=1OC)=[O:16])=O)(C)(C)C.C(=O)(OC1C=CC=CC=1)OCCCN(C)C>CN(C)C=O.C(OCC)(=O)C>[CH3:18][NH:17][C:15](=[O:16])[C:14]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:13]=1

Participants

5

Reactant 2

HCID 18791255HCID 18791255, compoundHCID 18791393HCID 18791393, compound

Product 1

HCID 11954N-MethylbenzamideYield 250.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-[2-[3-(tert-butoxycarbonylamino)prop-1-yl]oxybenzoyl]amino-3-methoxy-N-[2-(4-aminobut-1-yl)oxy-4-methylphenyl]-N-methylbenzamide (120 mg) and 3-(dimethylamino)prop-1-yl phenyl carbonate (127 mg) in N,N-dimethylformamide (5 ml) was stirred at 50° C. for 8 hours. The reaction mixture was diluted with ethyl acetate (15 ml) and the solution was washed successively with saturated aqueous sodium bicarbonate solution and brine. The solution was dried over potassium carbonate. The solvent was evaporated and the residue was purified on silica gel column chromatography (SiO2 20 g, 3-15% methanol in chloroform) to give 4-[2-[3-(tert-butoxycarbonylamino)prop-1-yl]oxybenzoyl]amino-3-methoxy-N-[2-(3-dimethylaminoprop-1-yl)oxycarbonylamino]but-1-yl]oxy-4-methylphenyl]-N-methylbenzamide (64 mg).

Workup

  1. washthe solution was washed successively with saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialThe solution was dried over potassium carbonate
  3. customThe solvent was evaporated
  4. customthe residue was purified on silica gel column chromatography (SiO2 20 g, 3-15% methanol in chloroform)

Sources & evidence

ORD record
ord-2a5270a591fe4283ab5f1609b1f96fe0
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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