Acetic acid, sodium salt, monohydrate → HCID 178487712, compound

HRID 1965932Notes

Reaction equation

HRID 1965932 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[C:4]([N:14]2[CH:18]=[CH:17][C:16]([NH:19][CH:20]([CH3:22])[CH3:21])=[N:15]2)[CH:3]=1.O.C([O-])(=[O:26])C.[Na+]>C(O)(=O)C>[OH:26][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[C:4]([N:14]2[CH:18]=[CH:17][C:16]([NH:19][CH:20]([CH3:22])[CH3:21])=[N:15]2)[CH:3]=1

Participants

4

Reactant 2

HCID 23681166Acetic acid, sodium salt, monohydrateHCID 57909998[1-(4-chloro-7-methoxy-quinolin-2-yl)-1H-pyrazol-3-yl]-isopropyl-amine

Product 1

HCID 178487712HCID 178487712, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of [1-(4-chloro-7-methoxy-quinolin-2-yl)-1H-pyrazol-3-yl]-isopropyl-amine (0.52 g, 1.6 mmol) and sodium acetate monohydrate (1.0 g) in acetic acid (5 mL) was stirred at 130° C. for 2 d. The mixture was concentrated and then partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate/hexanes), affording [1-(4-hydroxy-7-methoxy-quinolin-2-yl)-1H-pyrazol-3-yl]-isopropyl-amine (0.09 g, 19%). LC/MS=299.1 (M++1).

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between ethyl acetate (50 mL) and water (50 mL)
  3. concentrationThe organic layer was concentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-09e130064b0445f3acbd5729b4efac40
Source dataset
uspto-grants-2013_04
Patent number
US08420597B2

Reaction notes

Loading…