HCID 66748578, compound → HCID 66748385, compound

HRID 1622696Notes

Reaction equation

HRID 1622696 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:16][CH:15]=2)[C:5]2[N:10]([CH:11]=1)[CH2:9][CH2:8][S:7](=[O:13])(=[O:12])[N:6]=2>C1COCC1.CO.[Pt](=O)=O>[CH3:1][CH:2]1[CH2:11][N:10]2[C:5](=[N:6][S:7](=[O:13])(=[O:12])[CH2:8][CH2:9]2)[CH:4]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:16][CH:15]=2)[CH2:3]1

Participants

5

Reactant 1

HCID 66748578HCID 66748578, compound

Product 1

HCID 66748385HCID 66748385, compoundYield 24.8%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalyst2×HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of NaH (60%, 229 mg) in THF (dry) (10 mL) was added 2-chloroethanesulfonyl chloride (0.361 mL) at 0° C. and the mixture was stirred for 5 min at the same temperature. A solution of 5-methyl-3-(4-phenoxyphenyl)pyridin-2-amine (316 mg) in THF (dry) (20 mL) was added at 0° C. and the mixture was stirred at room temperature for 30 min. The mixture was quenched with water. Water and EtOAc were added and the extracted organic layer was washed with brine. Silica-gel was added and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (silica gel, eluted with MeOH in EtOAc) to give 7-methyl-9-(4-phenoxyphenyl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (158.2 mg) as a white solid. Platinum(IV) oxide (30.0 mg) was added to a solution of 7-methyl-9-(4-phenoxyphenyl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (141 mg) in THF (dry) (15 mL) and MeOH (15 mL) and the mixture was stirred at 50° C. under hydrogen overnight. Platinum(IV) oxide (30.0 mg) was added and the mixture was stirred at 50° C. under hydrogen for 1 day. The insoluble material was removed by filtration, silica-gel was added and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (silica gel, eluted with MeOH in EtOAc) and crystallized from THF/IPE to give the title compound (35.4 mg) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at 50° C. under hydrogen for 1 day
  2. customThe insoluble material was removed by filtration, silica-gel
  3. additionwas added
  4. customthe volatiles were removed in vacuo
  5. customwas purified by column chromatography (silica gel, eluted with MeOH in EtOAc)
  6. customcrystallized from THF/IPE

Sources & evidence

ORD record
ord-bd18e707f93e46018e1b28388f4cc328
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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