6-Piperazino-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine → 6-[4-[(2,2-Difluoro-1,3-benzodioxol-4-yl)methyl]piperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine

HRID 1674832Notes

Reaction equation

HRID 1674832 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.[F:20][C:21]1([F:32])[O:25][C:24]2[CH:26]=[CH:27][CH:28]=[C:29]([CH:30]=O)[C:23]=2[O:22]1>>[F:32][C:21]1([F:20])[O:25][C:24]2[CH:26]=[CH:27][CH:28]=[C:29]([CH2:30][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)[C:23]=2[O:22]1

Participants

3

Reactant 2

HCID 14768626-Piperazino-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazineHCID 27369702,2-Difluoro-benzo(1,3)dioxole-4-carbaldehyde

Product 1

HCID 673401976-[4-[(2,2-Difluoro-1,3-benzodioxol-4-yl)methyl]piperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine

Procedure

Reductive amination of 6-(piperazin-1-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine with 2,2-difluoro-1,3-benzodioxole-4-carbaldehyde was carried out according to General Synthetic Method 5. The crude product was purified by hplc using a Waters XBridge Prep C18 OBD column (5μ silica, 19 mm diameter, 100 mm length) eluted with decreasingly polar mixtures of water (containing 1% aqueous ammonia) and acetonitrile as eluents to give 6-[4-[(2,2-difluoro-1,3-benzodioxol-4-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 1% aqueous ammonia) and acetonitrile as eluents

Sources & evidence

ORD record
ord-6ccc57dae0d7458990803869f47ef868
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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