Triethylamine → N-[4-[(6,7-Dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepin-5-yl)carbonyl]3-chlorophenyl]3-fluoro-2-methylbenzamide

HRID 1420075Notes

Reaction equation

HRID 1420075 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[N:12]3[CH:19]=[CH:20][CH:21]=[C:11]3[CH2:10][CH2:9]2)=[O:7])=[C:4]([Cl:24])[CH:3]=1.C(N(CC)CC)C.[F:32][C:33]1[C:34]([CH3:42])=[C:35]([CH:39]=[CH:40][CH:41]=1)[C:36](Cl)=[O:37].[OH-].[Na+]>ClCCl>[CH:18]1[C:13]2[N:12]3[CH:19]=[CH:20][CH:21]=[C:11]3[CH2:10][CH2:9][N:8]([C:6]([C:5]3[CH:22]=[CH:23][C:2]([NH:1][C:36](=[O:37])[C:35]4[CH:39]=[CH:40][CH:41]=[C:33]([F:32])[C:34]=4[CH3:42])=[CH:3][C:4]=3[Cl:24])=[O:7])[C:14]=2[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 27792403-Fluoro-2-methylbenzoyl chlorideHCID 218369946,7-Dihydro-5-(4-amino-2-chlorobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepin

Product 1

HCID 21837130N-[4-[(6,7-Dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepin-5-yl)carbonyl]3-chlorophenyl]3-fluoro-2-methylbenzamideYield 106.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 0.10 g of 6,7-dihydro-5-(4-amino-2-chlorobenzoyl)-5H-pyrrolo-[1,2-a][1,5]benzodiazepine and 0.06 g of triethylamine in 6 ml of dichloromethane is added 0.08 g of 3-fluoro-2-methylbenzoyl chloride in 0.5 ml of dichloromethane. The mixture is stirred for 2 hours at room temperature and then 2 ml of 1N NaOH added. The volatiles are evaporated under vacuum and the residue dissolved in 2 ml of tetrahydrofuran and 1 ml of methanol. The mixture is stirred for 2 hours and evaporated and the residue diluted with 2 ml of 1N NaOH and 5 ml of water. The mixture is extracted with ethyl acetate (15 ml) and the extract washed with brine and dried (Na2SO4). The solvent is removed and the residue triturated with diethyl ether-hexane to give 0.15 g of white solid: Mass Spectrum (CI)474(M+H, Cl35); 476(M+H, Cl37).

Workup

  1. customThe volatiles are evaporated under vacuum
  2. dissolutionthe residue dissolved in 2 ml of tetrahydrofuran
  3. stirringThe mixture is stirred for 2 hours
  4. customevaporated
  5. additionthe residue diluted with 2 ml of 1N NaOH and 5 ml of water
  6. extractionThe mixture is extracted with ethyl acetate (15 ml)
  7. washthe extract washed with brine
  8. dry with materialdried (Na2SO4)
  9. customThe solvent is removed
  10. customthe residue triturated with diethyl ether-hexane

Sources & evidence

ORD record
ord-1289dde5b568473f9eea06c2240041b6
Source dataset
uspto-grants-1999_03
Patent number
US05889001

Reaction notes

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