Ethanol, 2-(aminooxy)- → HCID 89451604, compound

HRID 2175154Notes

Reaction equation

HRID 2175154 reaction equation
Cl.[O:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([S:19][C:20]2[N:24]4[CH:25]=[C:26]([C:29](=O)[CH3:30])[CH:27]=[CH:28][C:23]4=[N:22][N:21]=2)=[CH:14][CH:13]=3)[CH2:4][CH2:3]1.[NH2:32][O:33][CH2:34][CH2:35][OH:36]>CO.Cl>[OH:36][CH2:35][CH2:34][O:33]/[N:32]=[C:29](/[C:26]1[CH:27]=[CH:28][C:23]2[N:24]([C:20]([S:19][C:15]3[CH:16]=[C:17]4[C:12](=[CH:13][CH:14]=3)[N:11]=[CH:10][C:9]([CH2:8][N:5]3[CH2:6][CH2:7][O:2][CH2:3][CH2:4]3)=[CH:18]4)=[N:21][N:22]=2)[CH:25]=1)\[CH3:30]

Participants

5

Reactant 2

HCID 3014186Ethanol, 2-(aminooxy)-HCID 86696281HCID 86696281, compound

Product 1

HCID 89451604HCID 89451604, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 1-(3-(3-(morpholinomethyl)quinolin-6-ylthio)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethanone hydrochloride (79.3) (23 mg, 0.047 mmol) and 2-(aminooxy)ethanol (10.80 mg, 0.140 mmol) in MeOH (5 ml) was added 2 drops of HCl (2 N) by a 1-ml syringe to reach pH about 3 and the mixture was stirred in a sealed tube at 85° C. for 3 h. The mixture was evaporated to dryness and the residue was dissolved in water. The solution was neutralized by adding solid NaHCO3 until pH reached 9, then extracted by DCM (3×). The combined organic layers were washed by water again, dried over Na2SO4, filtered and evaporated. The residue was purified by preparative base HPLC (gradient eluent NB from 20/80 to 95/5. mobile phase A: NH4OH/CH3CN 0.04%; mobile phase B: NH4OH/H2O 0.04%). The desired fractions were collected, evaporated by BUCHI under 30 mbar at 35° C. to remove CH3CN. The remained solution was lyophilized to afford the title compound (12.2 mg, yield 54.2%).

Workup

  1. customThe mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in water
  3. additionby adding solid NaHCO3 until pH
  4. extractionextracted by DCM (3×)
  5. washThe combined organic layers were washed by water again
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by preparative base HPLC (gradient eluent NB from 20/80 to 95/5. mobile phase A: NH4OH/CH3CN 0.04%; mobile phase B: NH4OH/H2O 0.04%)
  10. customThe desired fractions were collected
  11. customevaporated by BUCHI under 30 mbar at 35° C.
  12. customto remove CH3CN

Sources & evidence

ORD record
ord-ccd8028640ae46a9a20111f4c1bb0550
Source dataset
uspto-grants-2015_06
Patent number
US09062045B2

Reaction notes

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