Methyl morpholine oxide → HCID 86676738, compound

HRID 2199314Notes

Reaction equation

HRID 2199314 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:10][C:11](=[O:30])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[C:14]([C:26]([F:29])([F:28])[F:27])[CH:13]=2)[CH:6]=[CH:7][C:8]=1[CH3:9].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH:2]([C:3]1[CH:4]=[C:5]([NH:10][C:11](=[O:30])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]3)=[C:14]([C:26]([F:29])([F:28])[F:27])[CH:13]=2)[CH:6]=[CH:7][C:8]=1[CH3:9])=[O:1]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 67326247HCID 67326247, compound

Product 1

HCID 86676738HCID 86676738, compoundYield 88,770.797%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-(3-(hydroxymethyl)-4-methylphenyl)-4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamide (200 mg, 0.47 mmol) in CH2Cl2 (2 mL) was added freshly dried 4 Å MS and NMO (83 mg, 0.71 mmol). The mixture was stirred for 10 min before TPAP (17 mg, 0.05 mmol) was added, and the resulting reaction mixture was stirred 12 hours at room temperature. The reaction mixture was filtered through celite, concentrated under reduced pressure, and purified by flash column chromatography (3% to 7% MeOH/CH2Cl2) to afford title product (175 g, 88% yield). MS m/z: 420 [M+1].

Workup

  1. additionwas added
  2. customthe resulting reaction mixture
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash column chromatography (3% to 7% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-0a386220c1724b63a2f33019893d9b15
Source dataset
uspto-grants-2016_06
Patent number
US09358231B2

Reaction notes

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