Ammonia → 2-(2,6-Dimethoxypyridin-4-yl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

HRID 1772933Notes

Reaction equation

HRID 1772933 reaction equation
Cl[C:2]1[C:7]([S:8](Cl)(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[C:18]([NH2:20])[CH:17]=[C:16]([O:21][CH3:22])[N:15]=1.N.[C:24](N1C=CN=C1)([N:26]1C=CN=C1)=[O:25]>N1C=CC=CC=1.ClCCCl>[CH3:22][O:21][C:16]1[CH:17]=[C:18]([N:20]2[C:24](=[O:25])[NH:26][C:2]3[N:3]=[CH:4][CH:5]=[CH:6][C:7]=3[S:8]2(=[O:10])=[O:9])[CH:19]=[C:14]([O:13][CH3:12])[N:15]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 102199682-Chloropyridine-3-sulfonyl chlorideHCID 222201912,6-Dimethoxypyridin-4-amine

Product 1

HCID 900547912-(2,6-Dimethoxypyridin-4-yl)-2H-pyrido[2,3-e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxideYield 20.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 1049PyridineSolvent

Procedure

The title compound (2.6 g, 7.73 mmol) was prepared in three steps from 2-chloropyridine-3-sulfonyl chloride (8.24 g, 38.9 mmol) and 2,6-dimethoxypyridin-4-amine (6.0 g, 38.9 mmol) in pyridine (25 mL) at rt; followed by ammonia in an autoclave at 100° C. for 16 h; followed by 1,1′-carbonyldiimidazole (6.2 g, 38.2 mmol) in 1,2-dichloroethane (100 mL) at 90° C. for 16 h using the methods of (IntF1), steps 1 and 2, and (IntA14), step 3.

Sources & evidence

ORD record
ord-2dcd85fadca244248e3d51d403f277d4
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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