4-Methylpiperidine-1-carbonyl Chloride → HCID 11594650, compound

HRID 2427832Notes

Reaction equation

HRID 2427832 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[OH:13])([O-:3])=[O:2].[CH3:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21](Cl)=[O:22])[CH2:17][CH2:16]1>N1C=CC=CC=1>[CH3:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:13][C:7]2[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[NH:9][N:8]=2)=[O:22])[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 152215164-Methylpiperidine-1-carbonyl ChlorideHCID 178526496HCID 178526496, compound

Product 1

HCID 11594650HCID 11594650, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

200 mg (1.12 mmol) of 5-nitro-1H-indazol-3-ol and 180.4 mg (1.67 mmol) of 4-methylpiperidine-1-carbonyl chloride (Example 2) in 20 ml of pyridin were heated under reflux for 5 h and left to stand overnight. 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: 48 mg (14%), M+H+: 304.99.

Workup

  1. temperatureunder reflux for 5 h
  2. waitleft
  3. distillationPyridine was distilled off in vacuo
  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-ab4cdad33a9c4cbca48267dbe3edb95f
Source dataset
uspto-grants-2011_06
Patent number
US07968719B2

Reaction notes

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