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

HRID 1420055Notes

Reaction equation

HRID 1420055 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[N:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:31][C:32]1[C:33]([CH3:41])=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35](Cl)=[O:36]>ClCCl>[N:19]1[N:11]2[C:10]([CH2:9][N:8]([C:6]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:35](=[O:36])[C:34]4[CH:38]=[CH:39][CH:40]=[C:32]([F:31])[C:33]=4[CH3:41])=[CH:23][CH:22]=3)=[O:7])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12]2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27792403-Fluoro-2-methylbenzoyl chlorideHCID 218371275,10-dihydro-5-(4-aminobenzoyl)-4H-pyrazolo[5,1-c][1,4]benzodiazepine

Product 1

HCID 21837157N-(4-(4H-Pyrazolo[5,1-c][1,4]benzodiazepin-5(10H)-ylcarbonyl)phenyl]-3-fluoro-2-methylbenzamideYield 105%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.25 g of 5,10-dihydro-5-(4-aminobenzoyl)-4H-pyrazolo[5,1-c][1,4]benzodiazepine and 0.0914 g of triethylamine in 6 ml of dichloromethane under argon is added a solution of 0.156 g of 3-fluoro-2-methylbenzoyl chloride in 1.5 ml of dichloromethane. The mixture is stirred overnight at room temperature and is washed with H2O and saturated NaHCO3. The organic layer is treated with activated carbon and filtered through magnesium sulfate. The filtrate is evaporated, ethyl acetate added and the solvent removed to give 0.38 g of white crystals, m.p. 245°-250° C.: Exact mass by mass spectrometry--441.1720(M+H).

Workup

  1. washis washed with H2O and saturated NaHCO3
  2. additionThe organic layer is treated with activated carbon
  3. filtrationfiltered through magnesium sulfate
  4. customThe filtrate is evaporated
  5. additionethyl acetate added
  6. customthe solvent removed

Sources & evidence

ORD record
ord-30ebb9c06b214d4383f4dd1f93e4ee22
Source dataset
uspto-grants-1999_03
Patent number
US05889001

Reaction notes

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