4-Methylpiperidine-1-carbonyl Chloride → HCID 11608827, compound

HRID 490308Notes

Reaction equation

HRID 490308 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([OH:11])=[N:5][NH:6]2.[CH3:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19](Cl)=[O:20])[CH2:15][CH2:14]1>N1C=CC=CC=1>[CH3:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:11][C:4]2[C:3]3[C:7](=[CH:8][CH:9]=[CH:10][C:2]=3[F:1])[NH:6][N:5]=2)=[O:20])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 152215164-Methylpiperidine-1-carbonyl Chloride2×HCID 178518958HCID 178518958, compound

Product 1

HCID 11608827HCID 11608827, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

100 mg (0.66 mmol) of 4-fluoro-1H-indazol-3-ol and 116.8 mg (0.72 mmol) of 4-methylpiperidine-1-carbonyl chloride (Example 2) in 10 ml of pyridine were heated under reflux for 4 h and left to stand overnight. Addition of 24 mg of 4-methyl-piperidine-1-carbonyl chloride was followed by heating under reflux for a further 2 h while the pyridine was distilled off in vacuo, 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: 56 mg (31%), M+H+: 278.1.

Workup

  1. temperatureunder reflux for 4 h
  2. waitleft
  3. temperatureby heating
  4. distillationwas distilled off in vacuo
  5. dissolutionthe residue was dissolved in water
  6. extractionextracted with ethyl acetate
  7. concentrationThe organic phase was concentrated
  8. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-e8f003b8843547d280f5e1beb62d127b
Source dataset
uspto-grants-2009_05
Patent number
US07528155B2

Reaction notes

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