Pyrrolidine → HCID 20554376, compound

HRID 1106028Notes

Reaction equation

HRID 1106028 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:7][C:8]([N:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]([CH3:21])[C:13](=[O:22])[C:12]2[CH:23]=[N:24][C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:26][C:11]1=2)=[O:9]>C1(C)C=CC=CC=1>[CH3:21][N:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:10]([C:8](=[O:9])[CH2:7][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:11]2[N:26]=[C:25]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:24]=[CH:23][C:12]=2[C:13]1=[O:22]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 20554372HCID 20554372, compound

Product 1

HCID 20554376HCID 20554376, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.35 g (19 mmol) of pyrrolidine are added slowly at 40° C. to a solution of 3 g (7 mmol) of 11-chloroacetyl-6-methyl-2-phenyl-5,6-dihydropyrimido[4,5-b][1,5]benzodiazepin-5-one in 30 ml of absolute toluene, while stirring. The mixture is stirred for a further 6 hours at 60° C. After filtration the solvent is removed on a rotary evaporator, and the residue is purified by chromatography on neutral silica gel using 99:1 chloroform/methanol as the eluant. After removing the solvent, the residue is stirred with methanol and finally recrystallized from ethanol; yield 1.1 g (34%), m.p. 196° C.

Workup

  1. stirringThe mixture is stirred for a further 6 hours at 60° C
  2. filtrationAfter filtration the solvent
  3. customis removed on a rotary evaporator
  4. customthe residue is purified by chromatography on neutral silica gel using 99:1 chloroform/methanol as the eluant
  5. customAfter removing the solvent
  6. stirringthe residue is stirred with methanol
  7. customfinally recrystallized from ethanol

Sources & evidence

ORD record
ord-0f8ee9543ecd41f3b410bc019744f2a5
Source dataset
uspto-grants-1982_01
Patent number
US04311700

Reaction notes

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