Acetone → HCID 117839216, compound

HRID 1477720Notes

Reaction equation

HRID 1477720 reaction equation
CC(C)=[O:3].[Cl:5][C:6]1[CH:32]=[CH:31][C:9]([CH2:10][N:11]2[CH:16]=[N:15][C:14]([NH:17][CH:18]3[CH2:22][CH2:21][C:20]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)=[CH:19]3)=[N:13][C:12]2=[O:30])=[CH:8][CH:7]=1.C[N+]1([O-])CCOCC1.S([O-])([O-])(=O)=S.[Na+].[Na+].[OH2:48]>[Os](=O)(=O)(=O)=O>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][N:11]2[CH:16]=[N:15][C:14]([NH:17][CH:18]3[CH2:22][CH2:21][C:20]([C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=4)([OH:48])[CH:19]3[OH:3])=[N:13][C:12]2=[O:30])=[CH:31][CH:32]=1

Participants

7

Reactant 5

HCID 180AcetoneHCID 962WaterHCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 117839819HCID 117839819, compound

Product 1

HCID 117839216HCID 117839216, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To an acetone (2.0 mL)-water (0.20 mL) solution of 1-(4-chlorobenzyl)-4-{[3-(4-fluorophenyl)cyclopent-2-en-1-yl]amino}-1,3,5-triazin-2(1H)-one (100 mg, 0.252 mmol) synthesized in Synthesis Example 121, immobilized osmium tetraoxide (32.0 mg, 0.0126 mmol, osmium content: 9.4%) was added and the resultant mixture was stirred at room temperature for 3 hours. Then, to the reaction solution, 4-methylmorpholine N-oxide (44.3 mg, 0.378 mmol) was added and the resultant mixture was stirred further for 3 days. After the completion of the reaction, to the reaction solution, saturated sodium thiosulfate aqueous solution was added and extraction with ethyl acetate from the reaction solution was performed. The organic layer was concentrated under reduced pressure and the resultant residue was purified by silica gel column chromatography (chloroform-ethyl acetate) to obtain the title compound (15.8 mg, yield: 12%).

Workup

  1. additionwas added
  2. customAfter the completion of the reaction
  3. extractionextraction with ethyl acetate from the reaction solution
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe resultant residue was purified by silica gel column chromatography (chloroform-ethyl acetate)

Sources & evidence

ORD record
ord-e593f6c7092d475099a63888c7b3782e
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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