1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazole-5-carbaldehyde → 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 1054940Notes

Reaction equation

HRID 1054940 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]=O)=[N:5][C:4]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[N:3]1.[Cl-].[CH3:15][C:16]1[N:21]2[N:22]=[C:23]([CH2:25][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:24]=[C:20]2[C:19]([CH3:45])=[N:18][CH:17]=1>>[CH:13]1([N:9]([C:4]2[N:5]=[C:6]([CH:7]=[CH:25][C:23]3[N:24]=[C:20]4[C:19]([CH3:45])=[N:18][CH:17]=[C:16]([CH3:15])[N:21]4[N:22]=3)[N:2]([CH3:1])[N:3]=2)[CH3:10])[CH2:11][CH2:12]1

Participants

3

Reactant 2

HCID 838754401-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazole-5-carbaldehydeHCID 86665503((5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)methyl)triphenylphosphonium chloride

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 52.6%

Procedure

Was prepared in the same manner as described in General Procedure Example 1g) using 1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazole-5-carbaldehyde (75 mg, 416 μmol, Eq: 1.00) and ((5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)methyl)triphenylphosphonium chloride (191 mg, 416 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 (71 mg, 52.6%) as light yellow solid. MS: m/z=325.4 (M+H+), mp: 196.4° C.

Workup

  1. customWas prepared in the same manner

Sources & evidence

ORD record
ord-d6482196e22d45b89d7b046ec46fa62a
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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