Tak-137 → 9-(4-Phenoxyphenyl)-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1405685Notes

Reaction equation

HRID 1405685 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:19]3=[N:20][S:21](=[O:25])(=[O:24])[CH2:22][CH2:23][N:18]3[CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.C(O)C.[C].[Rh].[Pt](=O)=O>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([CH:14]2[C:19]3=[N:20][S:21](=[O:25])(=[O:24])[CH2:22][CH2:23][N:18]3[CH2:17][CH2:16][CH2:15]2)=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 1

HCID 56649286Tak-137

Product 1

HCID 667484499-(4-Phenoxyphenyl)-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxideYield 87.4%

Reagents, catalysts & solvents 4

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

Procedure

A mixture of 9-(4-phenoxyphenyl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (173 mg) and 5% rhodium-carbon (50% wet, 17 mg) in THF (50 mL) and ethanol (20 mL) was stirred under a hydrogen atmosphere at room temperature overnight. To the reaction mixture was added platinum dioxide (17 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 7 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 (153 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 for 7 hr
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by aminopropyl silica-bound silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-062b89bc00634eed874f501d0f701e3f
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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