Ethanesulfonylchloride, 2-chloro- → 9-{2-[4-(1-Methylethyl)phenyl]ethyl}-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1747860Notes

Reaction equation

HRID 1747860 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[C:13]([NH2:18])=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][CH:5]=1)[CH3:3].[H-].[Na+].Cl[CH2:22][CH2:23][S:24](Cl)(=[O:26])=[O:25].C(=O)([O-])O.[Na+]>C1COCC1.C(OCC)(=O)C>[CH3:3][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]2[C:13]3=[N:18][S:24](=[O:26])(=[O:25])[CH2:23][CH2:22][N:14]3[CH:15]=[CH:16][CH:17]=2)=[CH:8][CH:9]=1)[CH3:1]

Participants

7

Reactant 4

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 641350373-{2-[4-(1-Methylethyl)phenyl]ethyl}pyridin-2-amine

Product 1

HCID 667480229-{2-[4-(1-Methylethyl)phenyl]ethyl}-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxideYield 72.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-{2-[4-(1-methylethyl)phenyl]ethyl}pyridin-2-amine (150 mg) in dehydrated THF (5 mL) was added to a mixture of sodium hydride (60%, 125 mg) and 2-chloroethanesulfonyl chloride (305 mg) in dehydrated THF (5 mL) under ice-cooling. The reaction mixture was stirred at room temperature for 2 hr, and saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added. The resulting precipitate was collected by filtration, and washed with water and ethyl acetate to give the title compound (149 mg) as a white solid. The obtained solid was crystallized from acetonitrile and diisopropyl ether to give a white solid.

Workup

  1. temperaturecooling
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water and ethyl acetate

Sources & evidence

ORD record
ord-86e4f64aa0304479aa8611a4dd64d74e
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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