Dimethylformamide → 1-[4-(6-(Methylamino)purin-9-yl)phenyl]-3-[3-(4-methylpiperazin-1-ylmethyl)-5-(trifluoromethyl)phenyl]urea

HRID 1912858Notes

Reaction equation

HRID 1912858 reaction equation
C[CH:2]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)[C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[NH2:6].[C:20](N1C=CN=C1)(N1C=CN=C1)=[O:21].[NH2:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]2[CH:47]=[N:46][C:45]3[C:40]2=[N:41][CH:42]=[N:43][C:44]=3[NH:48][CH3:49])=[CH:35][CH:34]=1.[CH3:50]N(C)C=O>ClCCl>[CH3:49][NH:48][C:44]1[N:43]=[CH:42][N:41]=[C:40]2[C:45]=1[N:46]=[CH:47][N:39]2[C:36]1[CH:37]=[CH:38][C:33]([NH:32][C:20]([NH:6][C:5]2[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=[C:3]([CH2:2][N:14]3[CH2:15][CH2:16][N:17]([CH3:50])[CH2:18][CH2:19]3)[CH:4]=2)=[O:21])=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 23155065[9-(4-aminophenyl)-9H-purin-6-yl]-methylamineHCID 693149873-(Methylpiperazin-1-ylmethyl)-5-(trifluoromethyl)aniline

Product 1

HCID 231552151-[4-(6-(Methylamino)purin-9-yl)phenyl]-3-[3-(4-methylpiperazin-1-ylmethyl)-5-(trifluoromethyl)phenyl]ureaYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 2 mL of dichloromethane, 608 mg (2.12 mmol) of 3-(methylpiperazin-1-ylmethyl)-5-(trifluoromethyl)aniline was dissolved, and 380 mg (2.34 mmol) of 1,1′-carbonylbis-1H-imidazole was added there to under cooling with ice, and the mixture solution was stirred at room temperature for three hours. To the reaction solution, 520 mg (2.16 mmol) of [9-(4-aminophenyl)-9H-purin-6-yl]-methylamine and 4 ml of dimethylformamide were added, and the mixture solution was further stirred at 40° C. for four hours. The residue obtained by concentrating the reaction solution was partitioned between water and ethyl acetate, and the organic layer was washed with a saturated sodium chloride solution and concentrated under reduced pressure. The product was recrystallized from ethyl acetate to obtain 742 mg (62%) of a target product as a white crystal.

Workup

  1. temperatureto under cooling with ice
  2. stirringthe mixture solution was further stirred at 40° C. for four hours
  3. customThe residue obtained
  4. concentrationby concentrating the reaction solution
  5. customwas partitioned between water and ethyl acetate
  6. washthe organic layer was washed with a saturated sodium chloride solution
  7. concentrationconcentrated under reduced pressure
  8. customThe product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d6698971f27d43bb88b62581f27b3f8d
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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