1,8-Diazabicyclo(5.4.0)undec-7-ene → 1H-pyrido[2,3-c][1,2,6]thiadiazin-4-amine-2,2-dioxide

HRID 471569Notes

Reaction equation

N[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[S:10]([NH2:14])([NH2:13])(=[O:12])=[O:11].C1CCN2C(=NCCC2)CC1>O>[NH:13]1[C:2]2[N:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]([NH2:5])=[N:14][S:10]1(=[O:12])=[O:11]

Participants

Conditions

Temperature: 160 °C

Procedure

A stirred mixture of 2-aminonicotinonitrile (238 mg, 2.0 mmol), sulfamide (192 mg, 2.0 mmol), and 1 mL of DBU was heated at 160° C. under nitrogen overnight. After it was cooled down to room temperature, the reaction mixture was diluted with water, and extracted three times with EtOAc. The aqueous layer was dried down under vacuum, and the residue was purified by chromatography on silica gel eluting with 15% MeOH in dichloromethane to give the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 6.87 (t, J=5.6 Hz, 1H), 7.95 (brs, 2H), 8.22 (d, J=5.2 Hz, 1H), 8.39-8.37 (m, 1H), 12.58 (brs, 1H). MS 199 (MH+).

Workup

temperatureAfter it was cooled down to room temperature
extractionextracted three times with EtOAc
customThe aqueous layer was dried down under vacuum
customthe residue was purified by chromatography on silica gel eluting with 15% MeOH in dichloromethane

Sources & evidence

ORD record: ord-33c9b5c725284376ba9477343a50ed9a
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633186B2

Reaction notes

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