Morpholine → N-[4-(5H-pyrrolo-[2,1-c][1,4]benzodiazepin10(11H)-ylcarbonyl)phenyl]4-morpholineacetamide

HRID 1740042Notes

Reaction equation

HRID 1740042 reaction equation
Cl[CH2:2][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].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.CN1CCCN(C)C1=O>C(Cl)Cl>[CH:27]1[CH:26]=[CH:25][N:17]2[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:14]([C:12]([C:9]3[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[CH2:2][N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:7][CH:8]=3)=[O:13])[CH2:15][C:16]=12

Participants

5

Reactant 3

HCID 8083MorpholineHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 218370752-chloro-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)ylcarbonyl)phenyl]acetamide

Product 1

HCID 70059534N-[4-(5H-pyrrolo-[2,1-c][1,4]benzodiazepin10(11H)-ylcarbonyl)phenyl]4-morpholineacetamideYield 106.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of 0.19 g of 2-chloro-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]acetamide in 1 ml of methylene chloride is added 0.44 g of morpholine followed by 1 ml of 1,3-di- methyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone and stirring continued for 20 hours. The methylene chloride is evaporated and the residue diluted with water. The resulting suspension is filtered and the precipitate washed with water. The brown solid is dissolved in 15 ml of ethyl acetate and washed with saturated NaHCO3, brine and dried with Na2SO4. The mixture is filtered and the filtrate evaporated in vacuo to give 0.23 g of a colorless gum which is stirred with ethyl acetate-hexanes to give 0.21 g of white solid. MS(CI): 431(M+H).

Workup

  1. customThe methylene chloride is evaporated
  2. additionthe residue diluted with water
  3. filtrationThe resulting suspension is filtered
  4. washthe precipitate washed with water
  5. dissolutionThe brown solid is dissolved in 15 ml of ethyl acetate
  6. washwashed with saturated NaHCO3, brine
  7. dry with materialdried with Na2SO4
  8. filtrationThe mixture is filtered
  9. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-b94f1e4b74144c2087f3b0720eb06fee
Source dataset
uspto-grants-1999_10
Patent number
US05968930

Reaction notes

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