HCID 57809749, compound → HCID 10072810, compound

HRID 2106028Notes

Reaction equation

HRID 2106028 reaction equation
[CH:1]1([CH:4]([OH:33])[C:5]2[CH:6]=[C:7]([C:11]([CH3:32])([CH3:31])[CH2:12][C:13]([OH:30])([C:26]([F:29])([F:28])[F:27])[CH2:14][N:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18](=[O:25])[CH:17]=[CH:16]3)[CH:8]=[CH:9][CH:10]=2)[CH2:3][CH2:2]1>C(Cl)Cl.O=[Mn]=O>[CH:1]1([C:4]([C:5]2[CH:6]=[C:7]([C:11]([CH3:32])([CH3:31])[CH2:12][C:13]([OH:30])([C:26]([F:27])([F:28])[F:29])[CH2:14][N:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18](=[O:25])[CH:17]=[CH:16]3)[CH:8]=[CH:9][CH:10]=2)=[O:33])[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 57809749HCID 57809749, compound

Product 1

HCID 10072810HCID 10072810, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-{4-[3-(cyclopropylhydroxymethyl)phenyl]-2-hydroxy-4-methyl-2-trifluoromethylpentyl}-1H-quinolin-4-one (26 mg, 0.057 mmol) and MnO2 (5 mg, 0.57 mmol) in methylene chloride (2 mL) was stirred for 48 hours at room temperature under an atmosphere of argon and filtered over CELITE® filter aid. The filtrate was concentrated in vacuo and the residue purified by reversed phase HPLC to afford 1-[4-(3-cyclopropanecarbonylphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one. Yield: 9 mg (35%).

Workup

  1. filtrationfiltered over CELITE®
  2. filtrationfilter aid
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue purified by reversed phase HPLC

Sources & evidence

ORD record
ord-52969d7fce0f48a7a28e94ab7c67f7d1
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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