6-Piperazino-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine → HCID 67341518, compound

HRID 1674888Notes

Reaction equation

HRID 1674888 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([C:16]([F:19])([F:18])[F:17])=[N:14][N:15]=3)[N:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([S:27][C:28]2[N:33]=[CH:32][C:31]([CH:34]=O)=[CH:30][CH:29]=2)=[CH:23][CH:22]=1>>[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([S:27][C:28]2[N:33]=[CH:32][C:31]([CH2:34][N:4]3[CH2:3][CH2:2][N:1]([C:7]4[CH:8]=[CH:9][C:10]5[N:11]([C:13]([C:16]([F:17])([F:18])[F:19])=[N:14][N:15]=5)[N:12]=4)[CH2:6][CH2:5]3)=[CH:30][CH:29]=2)=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 14768626-Piperazino-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazineHCID 1479480HCID 1479480, compound

Product 1

HCID 67341518HCID 67341518, compound

Procedure

Reductive amination of 6-(piperazin-1-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine with 6-(4-methylphenyl)sulfanylpyridine-3-carbaldehyde was carried out according to General Synthetic Method 7. The crude product was purified by hplc using a Waters XBridge Prep C18 OBD column, 5μ silica, 30 mm diameter, 100 mm length eluted with decreasingly polar mixtures of water (containing 0.1% aqueous ammonia) and acetonitrile as eluents to give 6-[4-[[6-(4-methylphenyl)sulfanylpyridin-3-yl]methyl]piperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine.

Workup

  1. customThe crude product was purified by hplc
  2. washeluted with decreasingly polar mixtures of water (containing 0.1% aqueous ammonia) and acetonitrile as eluents

Sources & evidence

ORD record
ord-ba28431ecfc84bd2863b9e294d41a916
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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