6-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazine → 1-[1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]-4H-3,1-benzoxazin-2-one

HRID 1674803Notes

Reaction equation

HRID 1674803 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][O:10][C:9]2=[O:18])[CH2:4][CH2:3]1.Cl[C:20]1[CH:21]=[CH:22][C:23]2[N:24]([C:26]([C:29]([F:32])([F:31])[F:30])=[N:27][N:28]=2)[N:25]=1>>[F:31][C:29]([F:30])([F:32])[C:26]1[N:24]2[N:25]=[C:20]([N:2]3[CH2:3][CH2:4][CH:5]([N:8]4[C:13]5[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=5[CH2:11][O:10][C:9]4=[O:18])[CH2:6][CH2:7]3)[CH:21]=[CH:22][C:23]2=[N:28][N:27]=1

Participants

3

Reactant 2

HCID 6136576-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazineHCID 220630891-(4-Piperidinyl)-1,2-dihydro-4H-3,1-benzoxazin-2-one hydrochloride

Product 1

HCID 673411941-[1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]-4H-3,1-benzoxazin-2-one

Procedure

A mixture of 1-piperidin-4-yl-4H-3,1-benzoxazin-2-one hydrochloride 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 XTerra C18 column (5μ silica, 19 mm diameter, 100 mm length) eluted with decreasingly polar mixtures of water (containing 0.1% aqueous ammonia) and acetonitrile as eluents to give 1-[1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]-4H-3,1-benzoxazin-2-one.

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 0.1% aqueous ammonia) and acetonitrile as eluents

Sources & evidence

ORD record
ord-c3aec14f46d744c5b53b8b232e953218
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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