Dimethylformamide → HCID 22118883, compound

HRID 1275020Notes

Reaction equation

HRID 1275020 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[CH2:12][C:13]([OH:15])=O.C(Cl)(=O)C(Cl)=O.CN(C)C=O.[CH3:27][O:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][C:30]=1[N:36]1[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]1>ClCCl.C(N(CC)CC)C>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[CH2:12][C:13]([NH:33][C:32]1[CH:34]=[CH:35][C:29]([O:28][CH3:27])=[C:30]([N:36]2[CH2:37][CH2:38][N:39]([CH3:42])[CH2:40][CH2:41]2)[CH:31]=1)=[O:15]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)anilineHCID 22118909HCID 22118909, compound

Product 1

HCID 22118883HCID 22118883, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

5-Bromo-1-naphthylacetic acid (Bull. Soc. Chim. Fr 1968, 71, 2957, 4.7 g, 17.8 mmol) in dichloromethane (150 ml) was treated with oxalyl chloride (4.7 ml, 53.4 mmol) and a drop of dimethylformamide under an atmosphere of argon with stirring for 1.5 hours. The reation was then concentrated in vacuo to a gum which was azeotroped with toluene to remove excess oxalyl chloride. The acid chloride was dissolved in dichloromethane (100 ml) and treated with 4-methoxy-3-(4-methylpiperazin-1-yl)aniline (EP 0533268A 1, 3.9 g, 17.8 mmol,) and triethylamine (2 ml) and the reaction stirred at room temp. overnight. The reaction was washed with saturated aqueous potassium carbonate solution, dried (Na2SO4) and concentrated in vacuo to give the title compound as needles from ethanol (3.7 g, 50%).

Workup

  1. concentrationThe reation was then concentrated in vacuo to a gum which
  2. customwas azeotroped with toluene
  3. customto remove excess oxalyl chloride
  4. dissolutionThe acid chloride was dissolved in dichloromethane (100 ml)
  5. washThe reaction was washed with saturated aqueous potassium carbonate solution
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57efd667a3bf4cb1bdcca37fa82e49fd
Source dataset
uspto-grants-2000_12
Patent number
US06159979

Reaction notes

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