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

HRID 2035787Notes

Reaction equation

HRID 2035787 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[F:10][C:11]1[CH:16]=[C:15]([C:17]2[C:18]([NH2:23])=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:14]=[CH:13][C:12]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>C1COCC1.CCCCCC>[F:10][C:11]1[CH:16]=[C:15]([C:17]2[C:18]3=[N:23][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:19]3[CH:20]=[CH:21][CH:22]=2)[CH:14]=[CH:13][C:12]=1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 962WaterHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 667488543-(2-Fluorobiphenyl-4-yl)pyridin-2-amine

Product 1

HCID 667488159-(2-Fluorobiphenyl-4-yl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxideYield 54%

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-(2-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 ethyl acetate, and dried under reduced pressure to give the title compound (0.724 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 ethyl acetate
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-d7094817414f4d0c8682cd8ce7f76be2
Source dataset
uspto-grants-2013_11
Patent number
US08575154B2

Reaction notes

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