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

HRID 2035788Notes

Reaction equation

HRID 2035788 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]3=[N:14][S:15](=[O:19])(=[O:18])[CH2:16][CH2:17][N:12]3[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][C:3]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1.CO.[C].[Rh].[Pt](=O)=O>[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[C:13]3=[N:14][S:15](=[O:18])(=[O:19])[CH2:16][CH2:17][N:12]3[CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 1

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

Product 1

HCID 667485189-(2-Fluorobiphenyl-4-yl)-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxideYield 59.9%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 178503043HCID 178503043, compoundCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 9-(2-fluorobiphenyl-4-yl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (200 mg) in THF/methanol (30 mL/30 mL) was added 5% rhodium carbon (50 mg). The reaction mixture was stirred under a hydrogen atmosphere at room temperature for 1 day. Platinum (IV) oxide (40 mg) was added, and the mixture was stirred under a hydrogen atmosphere at room temperature for 9 hr, and insoluble material was filtered off through celite. The filtrate was concentrated under reduced pressure, the obtained residue was purified by recrystallization (THF-ethyl acetate/diisopropyl ether) to give the title compound (121.2 mg).

Workup

  1. stirringthe mixture was stirred under a hydrogen atmosphere at room temperature for 9 hr
  2. filtrationinsoluble material was filtered off through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe obtained residue was purified by recrystallization (THF-ethyl acetate/diisopropyl ether)

Sources & evidence

ORD record
ord-ab5bf110e8d34ed4a1e82ea8246a3f1a
Source dataset
uspto-grants-2013_11
Patent number
US08575154B2

Reaction notes

Loading…