Potassium Carbonate → 4-(2,6-Difluoro-4-methoxybenzyl)-2-(6-methoxy-5-methylpyridin-3-yl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide

HRID 1772957Notes

Reaction equation

HRID 1772957 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:14](=[O:15])[NH:13][C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[S:10]2(=[O:21])=[O:20])=[CH:5][C:4]=1[CH3:22].[F:23][C:24]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[C:28]([F:34])[C:25]=1[CH2:26]Br.C([O-])([O-])=O.[K+].[K+].COC1C(C)=CC(N2C(=O)N(CC3C(F)=CC(F)=CC=3F)C3C=CC=CC=3S2(=O)=O)=CC=1C>CN(C=O)C>[F:23][C:24]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[C:28]([F:34])[C:25]=1[CH2:26][N:13]1[C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[S:10](=[O:21])(=[O:20])[N:9]([C:6]2[CH:7]=[N:8][C:3]([O:2][CH3:1])=[C:4]([CH3:22])[CH:5]=2)[C:14]1=[O:15]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 33542722,6-Difluoro-4-methoxybenzyl bromideHCID 727220852-(4-methoxy-3,5-dimethylphenyl)-4-(2,4,6-trifluorobenzyl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxideHCID 900551072-(6-methoxy-5-methylpyridin-3-yl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide

Product 1

HCID 727207774-(2,6-Difluoro-4-methoxybenzyl)-2-(6-methoxy-5-methylpyridin-3-yl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxideYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound (60 mg, 0.13 mmol) was prepared from 2-(6-methoxy-5-methylpyridin-3-yl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide (IntA28) (161 mg, 0.50 mmol), 2,6-difluoro-4-methoxybenzyl bromide (179 mg, 0.76 mmol) and K2CO3 (104 mg, 0.75 mmol) in DMF (3 mL) using the methods of (115).

Sources & evidence

ORD record
ord-ba0affdc10214aefa12539c7dcf4eb71
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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