Diisopropylethylamine → HCID 18506776, compound
Reaction equation
Cl.[CH2:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][NH:4][CH2:3]1.CCN(C(C)C)C(C)C.Cl[C:23]1[N:24]=[C:25]([S:31][CH3:32])[N:26]=[N:27][C:28]=1[C:29]#[N:30]>C(O)C>[CH3:32][S:31][C:25]1[N:26]=[N:27][C:28]([C:29]#[N:30])=[C:23]([N:4]2[CH2:3][CH2:2][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[CH2:6][CH2:5]2)[N:24]=1Participants
Procedure
A solution of 395 mg (2.7 mmol) of 2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride [J. Heterocycl. Chem. 1971, 8(5), 779-83] in 5 ml of ethanol was treated at room temperature with 0.92 ml (5.4 mmol) of Huenig's base and, thereupon, with a solution of 501 mg (2.7 mmol) of crude 5-chloro-3-methylsulfanyl-[1,2,4]triazine-6-carbonitrile in 5 ml of ethanol. The dark brown reaction mixture was stirred during 18 h at room temperature. For the working-up, the product, partially precipitated in pure form, was filtered and the resulting mother liquor evaporated under reduced pressure. The residue was chromatographed on silica gel with a 2:1 v/v mixture of hexane and ethylacetate as the eluent. In total, 470 mg (58.5% of theory) of 3-methylsulfanyl-5-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-[1,2,4]triazine-6-carbonitrile were obtained in the form of a beige powder; MS: 298 (M+H)+.
Workup
- customthe product, partially precipitated in pure form
- filtrationwas filtered
- customthe resulting mother liquor evaporated under reduced pressure
- customThe residue was chromatographed on silica gel with a 2:1 v/v mixture of hexane and ethylacetate as the eluent
Sources & evidence
- ORD record
- ord-b779771b4fd04f0f850506ad02bd5ed6
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06586422B2
Reaction notes
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