4,4,4-Trifluoro-1-(pyridin-4-yl)butane-1,3-dione → 2-[4-(Phenylmethyl)-1-piperazinyl]-7-(4-pyridinyl)-5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 482872Notes

Reaction equation

HRID 482872 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)=O.[NH2:16][C:17]1[C:21]([C:22]#[N:23])=[C:20]([N:24]2[CH2:29][CH2:28][N:27]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:26][CH2:25]2)[NH:19][N:18]=1>C(O)(=O)C>[C:31]1([CH2:30][N:27]2[CH2:28][CH2:29][N:24]([C:20]3[C:21]([C:22]#[N:23])=[C:17]4[N:16]=[C:3]([C:2]([F:15])([F:14])[F:1])[CH:4]=[C:5]([C:7]5[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=5)[N:18]4[N:19]=3)[CH2:25][CH2:26]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 2382984,4,4-Trifluoro-1-(pyridin-4-yl)butane-1,3-dioneHCID 1785104933-Amino-5-(4-benzyl-1-piperazinyl)-4-pyrazolecarbonitrile

Product 1

HCID 135799852-[4-(Phenylmethyl)-1-piperazinyl]-7-(4-pyridinyl)-5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3.9 g (0.014 moles) of 4,4,4-trifluoro-1-(4-pyridyl)-1,3-butanedione (U.S. Pat. No. 3,200,128), 3.9 g (0.014 moles) of 3-amino-5-(4-phenylmethyl-1-piperazinyl)-4-pyrazolecarbonitrile (prepared as described in Example 1) and 100 ml of glacial acetic acid was stirred at reflux for 16 hours.

Workup

  1. temperatureat reflux for 16 hours

Sources & evidence

ORD record
ord-6e38e4dde82f4b548ec27ee0dface164
Source dataset
uspto-grants-1986_03
Patent number
US04576943

Reaction notes

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