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

HRID 1456148

Reaction equation

HRID 1456148 reaction equation
Cl[CH:2]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([N:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][N:17]3[CH:25]=[CH:26][CH:27]=[C:16]3[CH2:15]2)=[O:13])=[CH:8][CH:7]=1)=[O:4].[CH3:34][NH:35][CH3:36].CN1CCCN(C)C1=O.C(OCC)(=O)C.CCCCCC>CO>[CH3:34][N:35]([CH3:36])[CH:2]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([N:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][N:17]3[CH:25]=[CH:26][CH:27]=[C:16]3[CH2:15]2)=[O:13])=[CH:8][CH:7]=1)=[O:4]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 21226206Ethyl acetate hexaneHCID 21837022alpha-Chloro-N-[4-(5H-pyrrolo[2,1-c][1,4)benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide

Product 1

HCID 21837078alpha-(Dimethylamino)-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A partial solution of ??g of α-chloro-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepine-10(11H)-ylcarbonyl)phenyl]benzeneacetamide in 1 ml of methanol is treated with 0.5 ml of dimethylamine and 1 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone and stirring continued for 20 hours. The methanol is evaporated and the residue diluted with water. The resulting solid is washed with water, dissolved in ethyl acetate and the organic layer washed with saturated NaHCO3, brine and dried with Na2SO4. The mixture is filtered and the filtrate evaporated in vacuo to give a residue which is stirred with ethyl acetate-hexane to give 0.15 g of a beige solid. MS(CI): 465(M+H).

Workup

  1. customThe methanol is evaporated
  2. additionthe residue diluted with water
  3. washThe resulting solid is washed with water
  4. dissolutiondissolved in ethyl acetate
  5. washthe organic layer washed with saturated NaHCO3, brine
  6. dry with materialdried with Na2SO4
  7. filtrationThe mixture is filtered
  8. customthe filtrate evaporated in vacuo
  9. customto give a residue which

Sources & evidence

ORD record
ord-edede3c4d66c4ac69a4356c7446eae38
Source dataset
uspto-grants-1998_12
Patent number
US05843944

Linked notes

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