1-(3-(Trifluoromethyl)phenyl)piperazine → 8-(1-{2-Oxo-2-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-ethyl}-1H-pyrazol-4-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

HRID 889053Notes

Reaction equation

HRID 889053 reaction equation
[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]3[CH:15]=[N:16][N:17]([CH2:19][C:20](Cl)=[O:21])[CH:18]=3)[NH:6][C:5]=2[C:4](=[O:23])[N:3]1[CH2:24][CH2:25][CH3:26].[F:27][C:28]([F:42])([F:41])[C:29]1[CH:30]=[C:31]([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH:32]=[CH:33][CH:34]=1>C1COCC1>[O:21]=[C:20]([N:38]1[CH2:37][CH2:36][N:35]([C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([C:28]([F:41])([F:42])[F:27])[CH:30]=2)[CH2:40][CH2:39]1)[CH2:19][N:17]1[CH:18]=[C:14]([C:7]2[NH:6][C:5]3[C:4](=[O:23])[N:3]([CH2:24][CH2:25][CH3:26])[C:2](=[O:1])[N:10]([CH2:11][CH2:12][CH3:13])[C:9]=3[N:8]=2)[CH:15]=[N:16]1

Participants

4

Reactant 2

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 57429672HCID 57429672, compound

Product 1

HCID 574296498-(1-{2-Oxo-2-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-ethyl}-1H-pyrazol-4-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dioneYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-pyrazol-1-yl]-acetyl chloride (100 mg, 0.26 mmol) in THF (10 ml) was added TEA (53 mg, 0.53 mmol) and 1-(3-Trifluoromethyl-phenyl)-piperazine (66 mg, 0.29 mmol) at 0° C. and the mixture was stirred overnight. The reaction mixture was concentrated and purified by HPLC to obtain 8-(1-{2-Oxo-2-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-ethyl}-1H-pyrazol-4-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (30 mg, 21%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-23f93b97fb704f25ba7f91cf9353b7e3
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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