Triethylamine → HCID 12001418, compound

HRID 1409987Notes

Reaction equation

HRID 1409987 reaction equation
[O:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([OH:10])=[N:2]1.[CH3:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18](Cl)=[O:19])[CH2:14][CH2:13]1.C(N(CC)CC)C>N1C=CC=CC=1>[CH3:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:10][C:3]2[C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[O:1][N:2]=2)=[O:19])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 152215164-Methylpiperidine-1-carbonyl Chloride2×HCID 178518993HCID 178518993, compound

Product 1

HCID 12001418HCID 12001418, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

125 mg (0.918 mmol) of isoxazolo[5,4-b]pyridin-3-ol, 178 mg (1.1 mmol) of 4-methylpiperidine-1-carbonyl chloride and 255 μl (1.84 mmol) of triethylamine were dissolved in 10 ml of pyridine and stirred at room temperature for 4 h. A further 89 mg (0.55 mmol) of 4-methylpiperidine-1-carbonyl chloride and 128 μl (0.92 mmol) of triethylamine were added, and stirring was continued at room temperature for 6 h. The reaction mixture was concentrated, and the residue was dissolved in water and extracted with ethyl acetate. The organic phase was concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 101 mg (42%), M+H+: 262.1.

Workup

  1. stirringstirring
  2. waitwas continued at room temperature for 6 h
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe residue was dissolved in water
  5. extractionextracted with ethyl acetate
  6. concentrationThe organic phase was concentrated
  7. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-40ad2396cb6548f7815d95e8a39a04fe
Source dataset
uspto-grants-2014_12
Patent number
US08921404B2

Reaction notes

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