((5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)methyl)triphenylphosphonium chloride → Cyclopropyl-{5-[2-(5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-vinyl]-1-methyl-1H-[1,2,4]triazol-3-yl}-methyl-amine

HRID 1054938Notes

Reaction equation

HRID 1054938 reaction equation
[Cl-].[CH3:2][C:3]1[N:8]2[N:9]=[C:10]([CH2:12][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:11]=[C:7]2[C:6]([CH3:32])=[N:5][CH:4]=1.[CH:33]1([N:36]([CH3:45])[C:37]2[N:41]=[C:40]([CH:42]=O)[N:39]([CH3:44])[N:38]=2)[CH2:35][CH2:34]1>>[CH:33]1([N:36]([C:37]2[N:41]=[C:40]([CH:42]=[CH:12][C:10]3[N:11]=[C:7]4[C:6]([CH3:32])=[N:5][CH:4]=[C:3]([CH3:2])[N:8]4[N:9]=3)[N:39]([CH3:44])[N:38]=2)[CH3:45])[CH2:34][CH2:35]1

Participants

3

Reactant 2

HCID 86665503((5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)methyl)triphenylphosphonium chlorideHCID 900180013-(cyclopropyl(methyl)amino)-1-methyl-1H-1,2,4-triazole-5-carbaldehyde

Product 1

HCID 123856144Cyclopropyl-{5-[2-(5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-vinyl]-1-methyl-1H-[1,2,4]triazol-3-yl}-methyl-amineYield 33.4%

Procedure

Was prepared in the same manner as described in General Procedure Example 1g) using ((5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)methyl)triphenylphosphonium chloride (127 mg, 277 μmol, Eq: 1.00) and 3-(cyclopropyl(methyl)amino)-1-methyl-1H-1,2,4-triazole-5-carbaldehyde (50 mg, 277 μmol, Eq: 1.00) as starting materials. Chromatography afforded Cyclopropyl-{5-[2-(5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-vinyl]-1-methyl-1H-[1,2,4]triazol-3-yl}-methyl-amine (30 mg, 33.3%) as light yellow waxy solid. MS: m/z=325.5 (M+H+)

Workup

  1. customWas prepared in the same manner

Sources & evidence

ORD record
ord-734e8398e6f147e1a6e11ac540a29f1d
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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