Pyrrolidine → HCID 20083156, compound

HRID 1609060Notes

Reaction equation

HRID 1609060 reaction equation
F[C:2]1[C:11]([F:12])=[CH:10][C:9]2[C:13](=[O:20])[C:14]([C:16]([O:18][CH3:19])=[O:17])=[CH:15][N:7]3[C:8]=2[C:3]=1[CH2:4][CH2:5][N:6]3[CH3:21].[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.C1CCN2C(=NCCC2)CC1>CN(C)C=O>[N:22]1([C:2]2[C:11]([F:12])=[CH:10][C:9]3[C:13](=[O:20])[C:14]([C:16]([O:18][CH3:19])=[O:17])=[CH:15][N:7]4[C:8]=3[C:3]=2[CH2:4][CH2:5][N:6]4[CH3:21])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 19788691HCID 19788691, compound

Product 1

HCID 20083156HCID 20083156, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2.92 g of the compound (6) obtained in Example 2 (1), 1.07 g of pyrrolidine and 2.25 g of 1,8-diazabicyclo[5.4.0]-7-undecene were added to 20 ml of N,N-dimethylformamide, and the solution was heated at 80° C. for 12 hours. The solvent was removed by distillation, and 100 ml of chloroform was added to the residue. After washing with water, the organic layer was separated from the solution. After drying over magnesium sulfate, the solvent was removed by distillation. To the residue, 50 ml of isopropyl ether was added, and the solid was filtered to obtain 2.60 g of the subject compound (122).

Workup

  1. customThe solvent was removed by distillation, and 100 ml of chloroform
  2. additionwas added to the residue
  3. washAfter washing with water
  4. customthe organic layer was separated from the solution
  5. dry with materialAfter drying over magnesium sulfate
  6. customthe solvent was removed by distillation
  7. additionTo the residue, 50 ml of isopropyl ether was added
  8. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-c4b7556ee56d47669777930ca2111521
Source dataset
uspto-grants-1995_03
Patent number
US05399553

Reaction notes

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