Ethanesulfonylchloride, 2-chloro- → HCID 66747700, compound

HRID 1622762Notes

Reaction equation

HRID 1622762 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[F:10][C:11]1[CH:31]=[CH:30][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:23]([NH2:29])=[N:24][CH:25]=[C:26]([CH3:28])[CH:27]=3)=[CH:18][CH:17]=2)=[CH:13][C:12]=1[O:32][CH3:33]>C1COCC1>[F:10][C:11]1[CH:31]=[CH:30][C:14]([O:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[C:23]4=[N:29][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:24]4[CH:25]=[C:26]([CH3:28])[CH:27]=3)=[CH:20][CH:21]=2)=[CH:13][C:12]=1[O:32][CH3:33]

Participants

5

Reactant 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 66748403HCID 66748403, compound

Product 1

HCID 66747700HCID 66747700, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (60%, 222 mg) in THF (dry) (20 mL) was added 2-chloroethanesulfonyl chloride (0.233 mL) at 0° C. and the mixture was stirred for 10 min at the same temperature. A solution of 3-(4-(4-fluoro-3-methoxyphenoxy)phenyl)-5-methylpyridin-2-amine (360 mg) in THF (dry) (20 mL) was added at 0° C. and the mixture was stirred at room temperature under nitrogen overnight. The mixture was quenched with water at 0° C. Water, EtOAc and THF were added to the mixture and the organic phase was separated. Silica-gel was added to the organic phase and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (silica gel, eluted with MeOH in EtOAc) and concentrated in vacuo to give 9-[4-(4-fluoro-3-methoxyphenoxy)phenyl]-7-methyl-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide as a white solid. This product was subjected to the next reaction without further purification. A part of the product was crystallized from EtOAc/IPE to give the title compound as a colorless solid.

Workup

  1. stirringthe mixture was stirred at room temperature under nitrogen overnight
  2. customThe mixture was quenched with water at 0° C
  3. additionWater, EtOAc and THF were added to the mixture
  4. customthe organic phase was separated
  5. additionSilica-gel was added to the organic phase
  6. customthe volatiles were removed in vacuo
  7. customwas purified by column chromatography (silica gel, eluted with MeOH in EtOAc)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b41d59151bc247cb879f7338d2a596de
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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