Piperazine → HCID 86624995, compound

HRID 2099306Notes

Reaction equation

HRID 2099306 reaction equation
[F:1][C:2]([F:32])([F:31])[CH2:3][O:4][CH2:5][CH2:6][N:7]1[C:15]2[C:14]([NH:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][N:18]=3)=[N:13][C:12](Cl)=[N:11][C:10]=2[C:9]([CH2:24][NH:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[N:8]1.[NH:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42]>CS(C)=O>[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42].[F:1][C:2]([F:32])([F:31])[CH2:3][O:4][CH2:5][CH2:6][N:7]1[C:15]2[C:14]([NH:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][N:18]=3)=[N:13][C:12]([N:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)=[N:11][C:10]=2[C:9]([CH2:24][NH:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[N:8]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 6422Trifluoroacetic acidHCID 57794495HCID 57794495, compound

Product 1

HCID 86624995HCID 86624995, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

1-(2-(2,2,2-trifluoroethoxy)ethyl)-3-((2,2,2-trifluoroethylamino)methyl)-5-chloro-N-(pyrimidin-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-7-amine (213 mg, 0.41 mmol) prepared in Step 1 and piperazine (152 mg, 1.8 mmol) were mixed in dimethyl sulfoxide (3.0 ml) in a reaction vial. The reaction mixture was heated at 120° C. for 10 hours. The reaction was cooled to room temperature and brought to acidic condition by adding trifluoroacetic acid. The crude reaction mixture was purified by reverse phase HPLC (5-95% acetonitrile in water with 0.05% trifluoroacetic acid) and lyophilized to give the title compound as a dark yellow solid (70 mg).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customThe crude reaction mixture
  3. customwas purified by reverse phase HPLC (5-95% acetonitrile in water with 0.05% trifluoroacetic acid)

Sources & evidence

ORD record
ord-fc01ccf603f244d39e33112893188434
Source dataset
uspto-grants-2009_08
Patent number
US07569572B2

Reaction notes

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