Hexachloroethane → 4,5-Dimethyl-3-(5-methyl-[1,3,4]oxadiazol-2-ylmethyl)-6-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyridazine

HRID 1480015Notes

Reaction equation

HRID 1480015 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][N:16]=3)[CH2:11][CH2:10]2)[N:5]=[N:4][C:3]=1[CH2:25][C:26]([NH:28][NH:29][C:30](=O)[CH3:31])=[O:27].C(N(C(C)C)CC)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC(Cl)(Cl)C(Cl)(Cl)Cl>C(#N)C>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:17][N:16]=3)[CH2:11][CH2:10]2)[N:5]=[N:4][C:3]=1[CH2:25][C:26]1[O:27][C:30]([CH3:31])=[N:29][N:28]=1

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 59191525Acetic acid N'-(2-{4,5-dimethyl-6-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyridazin-3-yl}-acetyl)-hydrazide

Product 1

HCID 591915294,5-Dimethyl-3-(5-methyl-[1,3,4]oxadiazol-2-ylmethyl)-6-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyridazineYield 7.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Acetic acid N′-(2-{4,5-dimethyl-6-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyridazin-3-yl}-acetyl)-hydrazide (114 mg, 0.248 mmol) is added to a round-bottom flask under N2 followed by acetonitrile (3 mL), diisopropylethylamine (0.27 mL, 1.43 mmol) and triphenylphosphine (115.5 mg, 0.44 mmol) and the reaction is stirred for 30 min. Hexachloroethane (77.5 mg, 0.329 mmol) is then added and the reaction is stirred for 16 h. The crude mixture is purified via HPLC (ammonium hydroxide as a modifier) to afford the title compound (8 mg, 7%).

Workup

  1. stirringthe reaction is stirred for 16 h
  2. customThe crude mixture is purified via HPLC (ammonium hydroxide as a modifier)

Sources & evidence

ORD record
ord-c7b636d3c2d14fcf85bf00d228d03003
Source dataset
uspto-grants-2016_08
Patent number
US09409871B2

Reaction notes

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