HCID 86704236, compound → HCID 86704235, compound

HRID 624090Notes

Reaction equation

HRID 624090 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([NH:20][C:21]([C:23]3[N:24]=[CH:25][O:26][C:27]=3[C:28]3[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=3)=[O:22])[CH:17]=[N:16]1)[CH2:7][CH2:6]2>CC(C)=O.O=[Mn]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([NH:20][C:21]([C:23]3[N:24]=[CH:25][O:26][C:27]=3[C:28]3[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=3)=[O:22])[CH:17]=[N:16]1)[CH:7]=[CH:6]2

Participants

4

Reactant 1

HCID 86704236HCID 86704236, compound

Product 1

HCID 86704235HCID 86704235, compoundYield 7.3%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 180AcetoneSolvent2×

Procedure

A solution of N-(1-(3-(5-methoxyindolin-1-yl)propyl)-1H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide (69 mg, 0.15 mmol) in acetone (1.0 mL) was added dropwise to a suspension of MnO2 (50 mg, 0.575 mmol) in acetone (0.5 mL). After stirring the dark reaction mixture for 18 h, the mixture was filtered over celite, rinsed with acetone and the solvent was removed under reduced pressure. Purification by prep. HPLC yielded the title compound (5 mg) as a brown oil. LC-MS conditions D: tR=1.12 min, [M+H]+=456.3.

Workup

  1. customthe dark reaction mixture for 18 h
  2. filtrationthe mixture was filtered over celite
  3. washrinsed with acetone
  4. customthe solvent was removed under reduced pressure
  5. customPurification by prep

Sources & evidence

ORD record
ord-9949946cb798495c9a0acb127d933d26
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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