Water → 9-(3-Fluorobiphenyl-4-yl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1747891Notes

Reaction equation

HRID 1747891 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[F:10][C:11]1[CH:12]=[C:13]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:14]=[CH:15][C:16]=1[C:17]1[C:18]([NH2:23])=[N:19][CH:20]=[CH:21][CH:22]=1.O>C1COCC1.CCCCCC>[F:10][C:11]1[CH:12]=[C:13]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:14]=[CH:15][C:16]=1[C:17]1[C:18]2=[N:23][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:19]2[CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 667480303-(3-Fluorobiphenyl-4-yl)pyridin-2-amine

Product 1

HCID 667480549-(3-Fluorobiphenyl-4-yl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxideYield 79.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a suspension of 60% sodium hydride (0.76 g) in THF (20 mL) was added 2-chloroethanesulfonyl chloride (1.85 g) under ice-cooling. The reaction mixture was stirred under ice-cooling for 5 min, and a solution of 3-(3-fluorobiphenyl-4-yl)pyridin-2-amine (1.0 g) in THF (20 mL) was added. The reaction mixture was stirred at room temperature overnight, and water and hexane were added under ice-cooling. The resulting solid was collected by filtration, washed with diisopropyl ether, and dried under reduced pressure to give the title compound (1.06 g).

Workup

  1. temperaturecooling
  2. temperaturecooling for 5 min
  3. stirringThe reaction mixture was stirred at room temperature overnight
  4. temperaturecooling
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with diisopropyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-62f8b657890845619e890d019b3322a2
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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