6-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazine → 6-[4-[(1R)-1-(4-fluorophenyl)ethyl]piperazin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine

HRID 1675007Notes

Reaction equation

HRID 1675007 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH3:9])=[CH:4][CH:3]=1.Cl[C:17]1[CH:18]=[CH:19][C:20]2[N:21]([C:23]([C:26]([F:29])([F:28])[F:27])=[N:24][N:25]=2)[N:22]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([N:10]2[CH2:11][CH2:12][N:13]([C:17]3[CH:18]=[CH:19][C:20]4[N:21]([C:23]([C:26]([F:27])([F:29])[F:28])=[N:24][N:25]=4)[N:22]=3)[CH2:14][CH2:15]2)[CH3:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6136576-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazineHCID 16748801(R)-1-(1-(4-Fluorophenyl)ethyl)piperazine

Product 1

HCID 591497986-[4-[(1R)-1-(4-fluorophenyl)ethyl]piperazin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazineYield 87%

Procedure

A mixture of (R)-1-[1-(4-fluorophenyl)ethyl]piperazine (obtained as described in J. Med. Chem. 2007, 50, 3528) and 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine was allowed to react by the method described in Example 306 to give 6-[4-[(1R)-1-(4-fluorophenyl)ethyl]piperazin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine in 87% yield.

Workup

  1. customto react by the method

Sources & evidence

ORD record
ord-74782aa63b8042edbd9f31b12f207a0e
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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