Diisopropylethylamine → N-[4-(4H-Pyrazolo[5,1-c][1,4]benzodiazepin-5(10H)-ylcarbonyl)-3-chlorophenyl]-5-fluoro-2-methylbenzamide

HRID 1739916Notes

Reaction equation

HRID 1739916 reaction equation
[N:1]1[N:10]2[C:4]([CH2:5][NH:6][C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9]2)=[CH:3][CH:2]=1.[F:15][C:16]1[CH:17]=[CH:18][C:19]([CH3:35])=[C:20]([CH:34]=1)[C:21]([NH:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[C:26]([Cl:33])[CH:25]=1)=[O:22].C(N(C(C)C)CC)(C)C>ClCCl>[N:1]1[N:10]2[C:4]([CH2:5][N:6]([C:28]([C:27]3[CH:31]=[CH:32][C:24]([NH:23][C:21](=[O:22])[C:20]4[CH:34]=[C:16]([F:15])[CH:17]=[CH:18][C:19]=4[CH3:35])=[CH:25][C:26]=3[Cl:33])=[O:29])[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9]2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10639786Benzoyl chloride, 2-chloro-4-[(5-fluoro-2-methylbenzoyl)amino]-HCID 130628255,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepine

Product 1

HCID 21837055N-[4-(4H-Pyrazolo[5,1-c][1,4]benzodiazepin-5(10H)-ylcarbonyl)-3-chlorophenyl]-5-fluoro-2-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.185 g of 5,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepine, 0.391 g of 4-[(5-fluoro-2-methylbenzoyl)amino]-2-chlorobenzoyl chloride and 0.158 g of diisopropylethylamine in 10 ml of dichloromethane is stirred at room temperature overnight. The mixture is washed with H2O, 1 N HCl, H2O, 1M NAHCO3, brine and dried (Na2SO4). The solution is passed through a thin pad of hydrous magnesium silicate and the filter cake washed with dichloromethane. The filtrate is again passed through a thin pad of hydrous magnesium silicate. The filtrate is concentrated and the solid crystallized from ethyl acetate to give crystals, m.p. 137-140° C.

Workup

  1. washThe mixture is washed with H2O, 1 N HCl, H2O, 1M NAHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. washthe filter cake washed with dichloromethane
  4. concentrationThe filtrate is concentrated
  5. customthe solid crystallized from ethyl acetate
  6. customto give crystals, m.p. 137-140° C.

Sources & evidence

ORD record
ord-55a5638c6e4f42e59c31870adb14a33d
Source dataset
uspto-grants-1999_10
Patent number
US05968937

Reaction notes

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