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

HRID 1598248Notes

Reaction equation

HRID 1598248 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 887MethanolSolvent2×

Procedure

A partial solution of ??g of α-chloro-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-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 15 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. customevaporated
  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-0e70da4ff05044d4afa4a687d960cdf2
Source dataset
uspto-grants-1998_04
Patent number
US05736540

Reaction notes

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