Urea → Lenalidomide

HRID 1525631Notes

Reaction equation

HRID 1525631 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([CH:12]([CH2:17]C(O)=O)[CH2:13][C:14](O)=O)[C:6]2=[O:11].[NH2:21][C:22](N)=[O:23].CN(C)C=[O:28]>>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([CH:12]1[CH2:13][CH2:14][C:22](=[O:23])[NH:21][C:17]1=[O:28])[C:6]2=[O:11]

Participants

4

Reactant 3

HCID 1176UreaHCID 6228DimethylformamideHCID 66823861HCID 66823861, compound

Product 1

HCID 216326LenalidomideYield 30%

Procedure

A mixture of 3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-glutaric acid (5 g) and urea (1.08 g) in N,N-dimethylformamide (25 ml) was stirred and heated under reflux for 3˜4 hours. The reaction mixture concentrated under reduced pressure at 60° C. and then was added into ice water by being stirred rapidly. After filter, the cake was washed with isopropanol. The crude product was recrystallized from isopropanol and active carbon to give 1.4 g of off-white target compound. Yield: 30%. mp: 252.1˜254.3° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3˜4 hours
  3. concentrationThe reaction mixture concentrated under reduced pressure at 60° C.
  4. additionwas added into ice water
  5. stirringby being stirred rapidly
  6. filtrationAfter filter
  7. washthe cake was washed with isopropanol
  8. customThe crude product was recrystallized from isopropanol and active carbon

Sources & evidence

ORD record
ord-2768206bee754b05bc90ef69bab71a0c
Source dataset
uspto-grants-2015_07
Patent number
US09085530B2

Reaction notes

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