9-(5-Phenylthiophen-2-yl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide → 9-(5-Phenylthiophen-2-yl)-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 2035789Notes

Reaction equation

HRID 2035789 reaction equation
[C:1]1([C:7]2[S:11][C:10]([C:12]3[C:17]4=[N:18][S:19](=[O:23])(=[O:22])[CH2:20][CH2:21][N:16]4[CH:15]=[CH:14][CH:13]=3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.C1COCC1.[C].[Pd].[C].[Rh].[Ru].[Pt](=O)=O>[C:1]1([C:7]2[S:11][C:10]([CH:12]3[C:17]4=[N:18][S:19](=[O:22])(=[O:23])[CH2:20][CH2:21][N:16]4[CH2:15][CH2:14][CH2:13]3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 1

HCID 667480239-(5-Phenylthiophen-2-yl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

Product 1

HCID 667488149-(5-Phenylthiophen-2-yl)-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxideYield 34.8%

Reagents, catalysts & solvents 6

HCID 23950RutheniumCatalystHCID 345198Adams' catalystCatalystHCID 178418390HCID 178418390, compoundCatalystHCID 178503043HCID 178503043, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10% palladium-carbon (50% wet, 12 mg) and 9-(5-phenylthiophen-2-yl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (120 mg) in ethanol (10 mL) and dehydrated THF (60 mL) was stirred under a hydrogen atmosphere at room temperature for 4 hr. To the reaction mixture was added 5% rhodium-carbon (50% wet, 12 mg) and the mixture was stirred under a hydrogen atmosphere at room temperature overnight, and under a hydrogen atmosphere (4 atm) for 6 hr. To the reaction mixture was added 5% ruthenium-alumina (12 mg) and the mixture was stirred under a hydrogen atmosphere at room temperature overnight. To the reaction mixture was added platinum dioxide (12 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 24 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by aminopropyl silica-bound silica gel column chromatography (ethyl acetate/methanol) to give the title compound (42.3 mg) as a white solid. The obtained solid was crystallized from acetonitrile and diisopropyl ether.

Workup

  1. stirringthe mixture was stirred under a hydrogen atmosphere at room temperature overnight
  2. waitunder a hydrogen atmosphere (4 atm) for 6 hr
  3. stirringthe mixture was stirred under a hydrogen atmosphere at room temperature overnight
  4. stirringthe mixture was stirred under a hydrogen atmosphere at room temperature for 24 hr
  5. filtrationThe reaction mixture was filtered through celite
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by aminopropyl silica-bound silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-601376496ee3495fb11987b7a970d646
Source dataset
uspto-grants-2013_11
Patent number
US08575154B2

Reaction notes

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