9-Biphenyl-4-yl-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide → 9-Biphenyl-4-yl-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 2035749Notes

Reaction equation

HRID 2035749 reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:12]3=[N:13][S:14](=[O:18])(=[O:17])[CH2:15][CH2:16][N:11]3[CH:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1>C1COCC1.[C].[Pd]>[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:2]=[CH:3][C:4]([CH:7]2[C:12]3=[N:13][S:14](=[O:17])(=[O:18])[CH2:15][CH2:16][N:11]3[CH2:10][CH2:9][CH2:8]2)=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 667489979-Biphenyl-4-yl-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

Product 1

HCID 667481379-Biphenyl-4-yl-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxideYield 104.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10% palladium-carbon (50% wet, 12 mg) and 9-biphenyl-4-yl-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (115 mg) in THF (50 mL) was stirred under a hydrogen atmosphere overnight. The reaction mixture was filtered, and the filtrate was concentrated to give the title compound (122 mg) as a white solid. The obtained solid was crystallized from acetonitrile, diisopropyl ether and hexane to give a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-cb6c4aa2ccc64ff2be3f46cc83ca9e6e
Source dataset
uspto-grants-2013_11
Patent number
US08575154B2

Reaction notes

Loading…