Pyrrolidine → pyrrolidino-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 2380242Notes

Reaction equation

HRID 2380242 reaction equation
C([N:3]1[C:9]2[N:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:7](=[O:14])[N:6](C)[C:5]2[CH:16]=[CH:17][C:18](OS(C(F)(F)F)(=O)=O)=[N:19][C:4]1=2)C.[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1>C(OCC)(=O)C>[N:28]1([C:18]2[CH:17]=[CH:16][C:5]3[C:4]([N:19]=2)=[N:3][C:9]2[N:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:7](=[O:14])[N:6]=3)[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 107160835,11-Dihydro-11-ethyl-5-methyl-2-trifluoromethanesulfonyloxy-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Product 1

HCID 131718781pyrrolidino-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5,11-Dihydro-11-ethyl-5-methyl-2-trifluoromethanesulfonyloxy-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.25 g) was dissolved in pyrrolidine (1 ml) and refluxed 30 min. The cooled solution was diluted with ethyl acetate, washed with water, and the organic phase was dried (anhydrous magnesium sulfate) and concentrated. The resulting oily residue was crystallized from ethyl acetate/hexane to provide 0.11 g of 5,11-dihydro-11-ethyl-5-methyl-2-n-(pyrrolidino-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one, m.p. 185°-188° C.

Workup

  1. temperaturerefluxed 30 min
  2. washwashed with water
  3. dry with materialthe organic phase was dried (anhydrous magnesium sulfate)
  4. concentrationconcentrated
  5. customThe resulting oily residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-fa1bcef2de084958b1cea21000e2dac9
Source dataset
uspto-grants-1994_11
Patent number
US05366972

Reaction notes

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