HCID 66620998, compound → HCID 66621155, compound

HRID 415326Notes

Reaction equation

HRID 415326 reaction equation
[N:1]12[CH2:8][C:5]([C:9]([NH:11][C:12]3[C:13](O)=[C:14]([CH:19]=[CH:20][CH:21]=3)[C:15]([O:17][CH3:18])=[O:16])=[O:10])([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH2:2]2>C(O)(=O)CC>[N:1]12[CH2:8][C:5]([C:9]3[O:10][C:13]4[C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=[CH:21][C:12]=4[N:11]=3)([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH2:2]2

Participants

3

Reactant 1

HCID 66620998HCID 66620998, compound

Product 1

HCID 66621155HCID 66621155, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

A solution of methyl 3-(1-azabicyclo[3.2.1]octane-5-carboxamido)-2-hydroxybenzoate (500 mg, 1.64 mmol) in proponic acid 10 ml) was heated to reflux for 2 days. The resulting solution was concentrated under vacuum, the crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 20:1 to 2:1), 100 mg methyl 2-(1-azabicyclo[3.2.1]octan-5-yl)benzo[d]oxazole-7-carboxylate was obtained. Yield: 21%. LC-MS (ESI) (m/z): 287 (M+1)+.

Workup

  1. temperatureto reflux for 2 days
  2. concentrationThe resulting solution was concentrated under vacuum
  3. customthe crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 20:1 to 2:1)

Sources & evidence

ORD record
ord-0d2f98d062cc4dc9a8ba2daa28522373
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

Loading…