Diisopropylethylamine → HCID 18753282, compound

HRID 1838213Notes

Reaction equation

Cl.[C:2]1([C:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH:13]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)C(C)C)C.Cl[C:24]1[N:25]=[C:26]([S:32][CH3:33])[N:27]=[N:28][C:29]=1[C:30]#[N:31]>O1CCOCC1>[CH3:33][S:32][C:26]1[N:27]=[N:28][C:29]([C:30]#[N:31])=[C:24]([N:11]2[CH2:10][CH:9]=[C:8]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:13][CH2:12]2)[N:25]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 130 mg (0.66 mmol) of 4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride in 5 ml of dioxane was treated at room temperature with 0.23 ml (1.32 mmol) of N-ethyl-diisopropylamine and, thereupon, with 112 mg (0.60 mmol) of crude 5-chloro-3-methylsulfanyl-[1,2,4]triazine-6-carbonitrile. The reaction mixture was stirred at 50° C. during 18 hours. For the working-up, the solution was evaporated under reduced pressure and the residue was chromatographed on silica gel with a 2:1 mixture of hexane and ethylacetate as the eluent. There were obtained 120 mg (0.34 mmol, 64.5% of theory) of 3-methylsulfanyl-5-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-[1,2,4]triazine-6-carbonitrile in the form of an orange powder; MS: [M+H]+=310.

Workup

customthe solution was evaporated under reduced pressure
customthe residue was chromatographed on silica gel with a 2:1 mixture of hexane and ethylacetate as the eluent

Sources & evidence

ORD record: ord-a40776f2d31647eba90c9caeb5422078
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06673795B2

Reaction notes

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