Potassium Carbonate → HCID 72720979, compound

HRID 1772961Notes

Reaction equation

HRID 1772961 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([N:11]2[C:16](=[O:17])[NH:15][C:14]3[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=3[S:12]2(=[O:23])=[O:22])[CH:4]=1.[F:24][C:25]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:29]([F:35])[C:26]=1[CH2:27]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:24][C:25]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:29]([F:35])[C:26]=1[CH2:27][N:15]1[C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[S:12](=[O:22])(=[O:23])[N:11]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[N:6]=2)[C:16]1=[O:17]

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 90054779HCID 90054779, compound

Product 1

HCID 72720979HCID 72720979, compoundYield 3.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from 2-(4,6-dimethoxypyridin-2-yl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide (IntA33) (101 mg, 0.3 mmol), 2,6-difluoro-4-methoxybenzyl bromide (85 mg, 0.36 mmol) and K2CO3 (124 mg, 0.9 mmol) in DMF (1.5 mL) using the methods of (115). After trituration with Et2O further purification by preparative HPLC (method C) yielded the title compound (7 mg, 0.01 mmol).

Workup

  1. customAfter trituration with Et2O further purification by preparative HPLC (method C)

Sources & evidence

ORD record
ord-94a0a609f1a94bfb94c2d23d4e61d4ec
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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