1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 90026195, compound

HRID 1054987Notes

Reaction equation

[CH3:1][N:2]1[C:6]([CH:7]=O)=[N:5][C:4]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[N:3]1.[Cl-].[CH3:16][C:17]1[N:22]2[N:23]=[C:24]([CH2:26][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:25]=[C:21]2[C:20]([CH3:46])=[N:19][CH:18]=1.C1CCN2C(=NCCC2)CC1>O1CCCC1>[CH3:16][C:17]1[N:22]2[N:23]=[C:24](/[CH:26]=[CH:7]/[C:6]3[N:2]([CH3:1])[N:3]=[C:4]([N:9]4[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]4)[N:5]=3)[N:25]=[C:21]2[C:20]([CH3:46])=[N:19][CH:18]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 1-methyl-3-(piperidin-1-yl)-1H-1,2,4-triazole-5-carbaldehyde (60 mg, 309 μmol, Eq: 1.00), ((5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)methyl)triphenylphosphonium chloride (142 mg, 309 μmol, Eq: 1.00) and DBU (51.7 mg, 51.2 μl, 340 μmol, Eq: 1.1) in tetrahydrofuran (15 ml) was stirred for 18 hours at 25° C. under argon. The crude material was applied on silica gel and purified by flash chromatography over a 20 g silica gel column using ethyl acetate/methanol 0-7% as eluent affording 5,8-dimethyl-2-[(E)-2-(2-methyl-5-piperidin-1-yl-2H-[1,2,4]triazol-3-yl)-vinyl]-[1,2,4]triazolo[1,5-a]pyrazine (56 mg, 53.6%) as a yellow solid. MS: m/z=339.5 (M+H+), MP: 186-188° C.

Workup

custompurified by flash chromatography over a 20 g silica gel column

Sources & evidence

ORD record: ord-9e02558086e540c28d5cdf8cc767d76f
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394311B2

Reaction notes

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