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

HRID 55231

Reaction equation

HRID 55231 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[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:31][CH:32]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:33](Cl)=[O:34]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Cl:31][CH:32]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:33]([NH: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[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][CH:3]=1)=[O:34]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 102902Chloro(phenyl)acetyl chlorideHCID 1082828010,11-dihydro-10(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 21837022alpha-Chloro-N-[4-(5H-pyrrolo[2,1-c][1,4)benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamideYield 106.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

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 etherhexane 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 etherhexane

Sources & evidence

ORD record
ord-bcbc63f9cf95413cbcfeda195ccbfe44
Source dataset
uspto-grants-1997_04
Patent number
US05624923

Linked notes

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