HCID 66748462, compound → HCID 66747623, compound

HRID 1748015Notes

Reaction equation

HRID 1748015 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:18]4=[N:19][S:20](=[O:24])(=[O:23])[CH2:21][CH2:22][N:17]4[CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)=[CH:4][C:3]=1[O:27][CH3:28]>C1COCC1.CO.[Pt](=O)=O>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([CH:13]3[C:18]4=[N:19][S:20](=[O:24])(=[O:23])[CH2:21][CH2:22][N:17]4[CH2:16][CH2:15][CH2:14]3)=[CH:11][CH:12]=2)=[CH:4][C:3]=1[O:27][CH3:28]

Participants

5

Reactant 1

HCID 66748462HCID 66748462, compound

Product 1

HCID 66747623HCID 66747623, compoundYield 30.2%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalyst2×HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Platinum(IV) oxide (30 mg) was added to a solution of 9-[4-(4-chloro-3-methoxyphenoxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (262.3 mg) in THF (dry) (60 mL) and MeOH (30 mL). The mixture was stirred at room temperature under hydrogen for 3 hr. Platinum(IV) oxide (30 mg) was added and the mixture was stirred at room temperature under hydrogen for 4 hr. The insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc) and the filtrate was concentrated in vacuo. MeCN (13 mL) was added and this mixture was purified by preparative HPLC (C18, eluted with water in acetonitrile containing 0.1% TFA). The desired fractions were neutralized with sat.NaHCO3 aq. and the mixture was extracted with EtOAc. The combined organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was crystallized from THF/IPE to give the title compound (80.1 mg) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at room temperature under hydrogen for 4 hr
  2. customThe insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc)
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionMeCN (13 mL) was added
  5. customthis mixture was purified by preparative HPLC (C18, eluted with water in acetonitrile containing 0.1% TFA)
  6. extractionNaHCO3 aq. and the mixture was extracted with EtOAc
  7. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was crystallized from THF/IPE

Sources & evidence

ORD record
ord-c3d99696198944c89c9aa5dc2db403d5
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

Loading…