HCID 60162757, compound → HCID 60163416, compound

HRID 624089Notes

Reaction equation

HRID 624089 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][N:9]2[CH2:12][CH2:13][CH2:14][N:15]2[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]2)=[CH:5][CH:4]=1>CC(C)=O.O=[Mn]=O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[CH2:12][CH2:13][CH2:14][N:15]2[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]2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 60162757HCID 60162757, compound

Product 1

HCID 60163416HCID 60163416, compoundYield 16.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 180AcetoneSolvent2×

Procedure

A solution of N-(1-(3-(6-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 (11 mg) as a redish solid. LC-MS conditions D: tR=1.14 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-ea9ab34613ad42719e05a98769e1e414
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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