6-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazine → 6-(5-Benzyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine

HRID 1674805Notes

Reaction equation

HRID 1674805 reaction equation
Br.Br.[CH2:3]([N:10]1[C@@H:15]2[CH2:16][C@@H:12]([NH:13][CH2:14]2)[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:18]1[CH:19]=[CH:20][C:21]2[N:22]([C:24]([C:27]([F:30])([F:29])[F:28])=[N:25][N:26]=2)[N:23]=1>>[CH2:3]([N:10]1[CH2:11][CH:12]2[CH2:16][CH:15]1[CH2:14][N:13]2[C:18]1[CH:19]=[CH:20][C:21]2[N:22]([C:24]([C:27]([F:28])([F:30])[F:29])=[N:25][N:26]=2)[N:23]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 6136576-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazineHCID 14612541(1R,4R)-6-benzyl-3,6-diazabicyclo[2.2.1]heptane dihydrobromide

Product 1

HCID 673417346-(5-Benzyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine

Procedure

A mixture of (1R,4R)-6-benzyl-3,6-diazabicyclo[2.2.1]heptane dihydrobromide and 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine was allowed to react by General Synthetic Method 4. 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 0.2% aqueous ammonia) and acetonitrile as eluents to give 6-(5-benzyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine.

Workup

  1. customto react by General Synthetic Method 4
  2. customThe crude product was purified by hplc
  3. washeluted with decreasingly polar mixtures of water (containing 0.2% aqueous ammonia) and acetonitrile as eluents

Sources & evidence

ORD record
ord-51f63d7351804ccf8551805a0f20658c
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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