Pyrrolidine → 1-[2-(9-Bromo-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indol-1-yl)-1-oxoethyl]pyrrolidine

HRID 1384822Notes

Reaction equation

HRID 1384822 reaction equation
[Br:1][C:2]1[C:3]2[C:4]3[C:15]([CH2:16][C:17](O)=[O:18])=[N:14][N:13]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:12](=[O:26])[C:5]=3[N:6]([CH3:11])[C:7]=2[CH:8]=[CH:9][CH:10]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:39]1[CH2:43][CH2:42][CH2:41][CH2:40]1>O>[Br:1][C:2]1[C:3]2[C:4]3[C:15]([CH2:16][C:17]([N:39]4[CH2:43][CH2:42][CH2:41][CH2:40]4)=[O:18])=[N:14][N:13]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:12](=[O:26])[C:5]=3[N:6]([CH3:11])[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 682631,1'-CarbonyldiimidazoleHCID 211837259-Bromo-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetic acid

Product 1

HCID 211837231-[2-(9-Bromo-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indol-1-yl)-1-oxoethyl]pyrrolidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The preparation is carried out as in Example 3.2, from 3.1 g (7.5 mmol) of 9-bromo-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetic acid, from 1.4 g of 1,1′-carbonylbis-1H-imidazole and from 0.7 ml of pyrrolidine. After reaction, water is added and the precipitate is collected by filtration and dried under reduced pressure. It is recrystallized from propan-2-ol and washed with ether and pentane. It is dried under reduced pressure. 2.3 g (4.9 mmol) of solid are obtained.

Workup

  1. additionis added
  2. filtrationthe precipitate is collected by filtration
  3. customdried under reduced pressure
  4. customIt is recrystallized from propan-2-ol
  5. washwashed with ether and pentane
  6. customIt is dried under reduced pressure

Sources & evidence

ORD record
ord-b19aadc7dde64da287d92b8d17023733
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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