Dimethylformamide → 4-(2,6-Difluoro-4-methoxybenzyl)-2-(2-methoxypyridin-4-yl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide

HRID 1772947Notes

Reaction equation

[C:1]([O-:4])([O-])=O.[K+].[K+].F[C:8]1C=[C:14]([O:16][CH3:17])[CH:13]=[C:12](F)[C:9]=1CBr.COC1C(C)=CC([N:28]2[C:33](=[O:34])[N:32]([CH2:35][C:36]3[C:41]([F:42])=[CH:40][C:39](F)=[CH:38][C:37]=3[F:44])[C:31]3[CH:45]=[CH:46][CH:47]=[CH:48][C:30]=3[S:29]2(=[O:50])=[O:49])=CC=1C.C[N:53](C=O)C>>[F:44][C:37]1[CH:38]=[C:39]([O:4][CH3:1])[CH:40]=[C:41]([F:42])[C:36]=1[CH2:35][N:32]1[C:31]2[CH:45]=[CH:46][CH:47]=[CH:48][C:30]=2[S:29](=[O:49])(=[O:50])[N:28]([C:12]2[CH:9]=[CH:8][N:53]=[C:14]([O:16][CH3:17])[CH:13]=2)[C:33]1=[O:34]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 11430Potassium Carbonate

HCID 33542722,6-Difluoro-4-methoxybenzyl bromide

HCID 727220852-(4-methoxy-3,5-dimethylphenyl)-4-(2,4,6-trifluorobenzyl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide

Product 1

HCID 727220874-(2,6-Difluoro-4-methoxybenzyl)-2-(2-methoxypyridin-4-yl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide

Procedure

The title compound (179 mg, 0.39 mmol) was prepared from (IntA4) (152 mg, 0.50 mmol), K2CO3 (207 mg, 1.5 mmol) and 2,6-difluoro-4-methoxybenzyl bromide (142 mg, 0.6 mmol) in DMF (5 mL) using the methods of (115).

Sources & evidence

ORD record: ord-61e6b8dccc3b45fc99d06a2aa6d207a1
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249160B2

Reaction notes

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