Triethylamine → alpha-Chloro-N-[4-(5H-pyrrolo[2,1-c][1,4)benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide

HRID 1740037Notes

Reaction equation

HRID 1740037 reaction equation
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]=[N:4][CH:3]=[CH:2]1.C([N:14]([CH2:17][CH3:18])CC)C.[Cl:19][CH:20]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:21](Cl)=[O:22].[C:30]([O-:33])(O)=O.[Na+]>C(Cl)Cl>[Cl:19][CH:20]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:21]([NH:14][C:17]1[CH:18]=[CH:8][C:7]([C:30]([N:1]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[CH2:5][N:4]3[CH:9]=[CH:10][CH:11]=[C:3]3[CH2:2]2)=[O:33])=[CH:6][CH:5]=1)=[O:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 102902Chloro(phenyl)acetyl chlorideHCID 1484311H-1,4-BenzodiazepineHCID 516892Sodium Bicarbonate

Product 1

HCID 21837022alpha-Chloro-N-[4-(5H-pyrrolo[2,1-c][1,4)benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.61 g of 10,11-dihydro-10(4-aminobenzoyl)-5H-pyrrolo][2,1-c][1,4]benzodiazepine in 8 ml of methylene chloride is added 0.30 g of triethylamine followed by 0.47 g of (±)-2-chloro-2-phenylacetyl chloride in 2 ml of methylene chloride. The mixture is stirred at room temperature for 1 hour and then diluted with 10 ml of 50% NaHCO3. The methylene chloride is evaporated and the residue is extracted with ethyl acetate. The separated organic layer is washed with saturated NaHCO3 and brine and then dried with Na2SO4 followed by filtering through a pad of hydrous magnesium silicate. The filtrate is evaporated to a residue which is stirred with ether-hexane to give 0.98 g of pink solid. MS(CI): 456(M+H).

Workup

  1. customThe methylene chloride is evaporated
  2. extractionthe residue is extracted with ethyl acetate
  3. washThe separated organic layer is washed with saturated NaHCO3 and brine
  4. dry with materialdried with Na2SO4
  5. filtrationby filtering through a pad of hydrous magnesium silicate
  6. customThe filtrate is evaporated to a residue which
  7. stirringis stirred with ether-hexane

Sources & evidence

ORD record
ord-9d05f96b86874db6be62f90be2669f62
Source dataset
uspto-grants-1999_10
Patent number
US05968930

Reaction notes

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