Pyrrolidine → HCID 21183753, compound

HRID 1384810Notes

Reaction equation

HRID 1384810 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:11])[C:6]3[C:12](=[O:26])[N:13]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:14]=[C:15]([CH2:16][C:17](O)=[O:18])[C:5]=3[C:4]=2[CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:39]1[CH2:43][CH2:42][CH2:41][CH2:40]1>O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:11])[C:6]3[C:12](=[O:26])[N:13]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:14]=[C:15]([CH2:16][C:17]([N:39]4[CH2:43][CH2:42][CH2:41][CH2:40]4)=[O:18])[C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 682631,1'-CarbonyldiimidazoleHCID 21183740HCID 21183740, compound

Product 1

HCID 21183753HCID 21183753, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.5 g (4 mmol) of 8-chloro-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetic acid and of 1.2 g (7.4 mmol) of 1,1′-carbonylbis-1H-imidazole in tetrahydrofuran is stirred for 1 h at 50° C. The mixture is cooled and an excess of pyrrolidine is added. After stirring for 15 h, the precipitate is collected by filtration, washed with water and with ether and recrystallized from propan-2-ol. 0.65 g (1.5 mmol) of solid is obtained.

Workup

  1. temperatureThe mixture is cooled
  2. filtrationthe precipitate is collected by filtration
  3. washwashed with water and with ether
  4. customrecrystallized from propan-2-ol

Sources & evidence

ORD record
ord-218d44ee37e94fc9bb132653f8ef9dad
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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