HCID 86722263, compound → HCID 178488263, compound

HRID 869418Notes

Reaction equation

HRID 869418 reaction equation
[Br:1][C:2]1[C:7]2[C:8]3[NH:9][CH:10]([C:16]4[N:17]=[C:18]([NH:21][C:22](=[O:26])[CH:23]([CH3:25])[CH3:24])[S:19][CH:20]=4)[CH2:11][C:12](=[O:15])[C:13]=3[O:14][C:6]=2[CH:5]=[CH:4][C:3]=1[O:27][CH3:28]>C1COCC1.O=[Mn]=O>[OH:15][C:12]1[CH:11]=[C:10]([C:16]2[N:17]=[C:18]([NH:21][C:22](=[O:26])[CH:23]([CH3:25])[CH3:24])[S:19][CH:20]=2)[N:9]=[C:8]2[C:7]3[C:2]([Br:1])=[C:3]([O:27][CH3:28])[CH:4]=[CH:5][C:6]=3[O:14][C:13]=12

Participants

4

Reactant 1

HCID 86722263HCID 86722263, compound

Product 1

HCID 178488263HCID 178488263, compoundYield 65.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 16B (1.1 g, 2.3 mmol) and MnO2 (6 g) in THF (20 mL) was heated to 110° C. and reacted overnight. TLC monitored the reaction. After the reaction completed, the reaction mixture was filtered and the filtrate was concentrated to give 16C (0.7 g, 63.9% yield).

Workup

  1. customreacted overnight
  2. customthe reaction
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5528cf74dfc54dfeac025641fb32599e
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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