Ethanesulfonic acid → HCID 25070764, compound

HRID 557285Notes

Reaction equation

HRID 557285 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][C:14]2[CH:18]=[C:17]([C:19]3[C:20]([NH2:25])=[N:21][CH:22]=[CH:23][CH:24]=3)[O:16][N:15]=2)=[CH:11][CH:10]=1.[CH2:28]([S:30]([OH:33])(=[O:32])=[O:31])[CH3:29]>CO>[CH2:28]([S:30]([OH:33])(=[O:32])=[O:31])[CH3:29].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][C:14]2[CH:18]=[C:17]([C:19]3[C:20]([NH2:25])=[N:21][CH:22]=[CH:23][CH:24]=3)[O:16][N:15]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 11668Ethanesulfonic acidHCID 16719049E-1210

Product 1

HCID 25070764HCID 25070764, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

3-(3-(4-(Pyridin-2-yloxymethyl)-benzyl)-isoxazol-5-yl)-pyridin-2-yl amine (200 mg) was dissolved in methanol (5 mL), and ethanesulfonic acid (47.8 μL) was added thereto at room temperature. This mixed solution was concentrated under a reduced pressure. To the residue thereof was added ethanol, and subjected to ultrasound treatment. Thereafter, this mixture was heated further to 60° C, and then, cooled to 0° C. To this mixed solution was added tert-butoxy methyl ether (5 mL), and subjected to ultrasound treatment. Thereafter, this mixture was heated further to 60° C, and then, cooled to 0° C. The precipitated solids were filtered, washed with a mixed solution of ethanol and tert-butoxy methyl ether (1:1), and then, in vacuo to obtain the title compound (195 mg).

Workup

  1. customat room temperature
  2. concentrationThis mixed solution was concentrated under a reduced pressure
  3. additionTo the residue thereof was added ethanol
  4. temperaturecooled to 0° C
  5. additionTo this mixed solution was added tert-butoxy methyl ether (5 mL)
  6. temperatureThereafter, this mixture was heated further to 60° C
  7. temperaturecooled to 0° C
  8. filtrationThe precipitated solids were filtered
  9. washwashed with a mixed solution of ethanol and tert-butoxy methyl ether (1:1)

Sources & evidence

ORD record
ord-3cead67f648c4fc7be9d167c079d7a81
Source dataset
uspto-grants-2011_11
Patent number
US08058444B2

Reaction notes

Loading…