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

HRID 711706Notes

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-faf7626a8be0443fa2e0cadfe0b37b05
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181276B2

Reaction notes

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