Diisopropylethylamine → 3-[Chloro(difluoro)methyl]-6-[4-(3,5-dichloropyridin-4-yl)piperazin-1-yl][1,2,4]triazolo[4,3-b]pyridazine

HRID 1675035Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([Cl:14])([F:13])[F:12])=[N:9][N:10]=2)[N:7]=1.[Cl:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([Cl:28])[C:21]=1[N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.CCN(C(C)C)C(C)C>C(O)C>[Cl:14][C:11]([F:13])([F:12])[C:8]1[N:6]2[N:7]=[C:2]([N:25]3[CH2:26][CH2:27][N:22]([C:21]4[C:20]([Cl:28])=[CH:19][N:18]=[CH:17][C:16]=4[Cl:15])[CH2:23][CH2:24]3)[CH:3]=[CH:4][C:5]2=[N:10][N:9]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 6-chloro-3-[chloro(difluoro)methyl]-[1,2,4]triazolo[4,3-b]pyridazine (obtained as described in Examples 335-338, preparation of starting materials) (53 mg, 0.22 mmol) in ethanol (1 mL) was added to 1-(3,5-dichloropyridin-4-yl)piperazine (77 mg, 0.33 mmol). The reaction mixture was treated with DIPEA (43 mg, 0.33 mmol) and the mixture was heated at 70° C. for 4 hours. The reaction mixture was evaporated to leave an involatile residue that was purified by preparative reverse phase chromatography to give 3-[chloro(difluoro)methyl]-6-[4-(3,5-dichloropyridin-4-yl)piperazin-1-yl][1,2,4]triazolo[4,3-b]pyridazine (28 mg, 29%).

Workup

customThe reaction mixture was evaporated
customto leave an involatile residue that
customwas purified by preparative reverse phase chromatography

Sources & evidence

ORD record: ord-af0762f060954731b83d1163e80eaaa6
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003649B2

Reaction notes

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