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

HRID 2405675Notes

Reaction equation

HRID 2405675 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-7f9ddaa4f2ad44f1a3df48d4193b4d42
Source dataset
uspto-grants-2014_08
Patent number
US08809266B2

Reaction notes

Loading…