Potassium Carbonate → HCID 72720776, compound

HRID 1772960Notes

Reaction equation

HRID 1772960 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][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])[N:4]=1.[F:24][C:25]1[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([F:34])[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>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][N:6]=[C:5]([N:11]2[C:16](=[O:17])[N:15]([CH2:27][C:26]3[C:25]([F:24])=[CH:32][C:31]([F:33])=[CH:30][C:29]=3[F:34])[C:14]3[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=3[S:12]2(=[O:23])=[O:22])[N:4]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 27770592,4,6-Trifluorobenzyl bromideHCID 727220852-(4-methoxy-3,5-dimethylphenyl)-4-(2,4,6-trifluorobenzyl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxideHCID 90054867HCID 90054867, compound

Product 1

HCID 72720776HCID 72720776, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from 2-(4,5-dimethoxypyrimidin-2-yl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide (IntA32) (50 mg, 0.15 mmol), 2,4,6-trifluorobenzyl bromide (41 mg, 0.18 mmol) and K2CO3 (62 mg, 0.45 mmol) in DMF (1.5 mL) using the methods of (115). After purification by gradient column chromatography further purification by preparative HPLC (method C) yielded the title compound (8 mg, 0.02 mmol).

Workup

  1. customAfter purification
  2. customby gradient column chromatography further purification by preparative HPLC (method C)

Sources & evidence

ORD record
ord-2edd01aae42d4537a901f5cce2716bf7
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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