1,1'-Carbonyldiimidazole → 2-(5,6-dimethoxypyridin-3-yl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

HRID 1772935Notes

Reaction equation

HRID 1772935 reaction equation
[NH2:1][C:2]1[C:7]([S:8]([NH:11][C:12]2[CH:13]=[N:14][C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=2)(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:22](N1C=CN=C1)(N1C=CN=C1)=[O:23]>ClCCCl>[CH3:19][O:18][C:16]1[CH:17]=[C:12]([N:11]2[C:22](=[O:23])[NH:1][C:2]3[N:3]=[CH:4][CH:5]=[CH:6][C:7]=3[S:8]2(=[O:10])=[O:9])[CH:13]=[N:14][C:15]=1[O:20][CH3:21]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 900305322-amino-N-(5,6-dimethoxypyridin-3-yl) pyridine-3-sulfonamide

Product 1

HCID 900548562-(5,6-dimethoxypyridin-3-yl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxideYield 64.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The title compound (1.4 g, 4.16 mmol) was prepared from 2-amino-N-(5,6-dimethoxypyridin-3-yl)pyridine-3-sulfonamide (2.0 g, 6.44 mmol) and 1,1′-carbonyldiimidazole (3.13 g, 19.3 mmol) in 1,2-dichloroethane (15 mL) at 90° C. for 16 h using the methods of (IntA14) step 3.

Sources & evidence

ORD record
ord-507c0ce2520b416ba9f16736568ab323
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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