Toluene → HCID 22933850, compound

HRID 1269766Notes

Reaction equation

HRID 1269766 reaction equation
O1CCOCC1.[ClH:7].[NH:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([NH:19][CH2:20][CH:21]3[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]3)=[O:18])=[CH:14][CH:15]=2)[CH:10]=[N:9]1.C1(C)C=CC=CC=1>O1CCOCC1.C(O)(=O)C>[ClH:7].[NH:24]1[CH2:25][CH2:26][CH:21]([CH2:20][NH:19][C:17]([C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[NH:8][N:9]=[CH:10]3)=[O:18])[CH2:22][CH2:23]1

Participants

6

Reactant 3

HCID 1140TolueneHCID 184475431,1-Dimethylethyl 4-[[(1H-indazol-5-ylcarbonyl)amino]methyl]-1-piperidinecarboxylateHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 22933850HCID 22933850, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A 4N-hydrogen chloride-1,4-dioxane solution (0.200 mg, 0.800 mmol) was added to a solution of tert-butyl 4-{[(1H-indazol-5-ylcarbonyl)amino]methyl}piperidine-1-carboxylate (36.0 mg, 0.100 mmol) in a mixture of 1,4-dioxane (0.4 ml) and acetic acid (0.7 ml) at room temperature, and the resulting mixture was stirred for 3 hours while being maintained at room temperature. Toluene was added to the reaction solution and the resulting mixture was stirred while being maintained at room temperature. Then, the resulting slurry was collected by filtration and dried under reduced pressure, and the resulting crude product residue was stirred in methanol (3.0 ml) for 1 hour with heating under reflux while maintaining the temperature. The resulting mixture was concentrated to dryness to obtain N-(piperidin-4-ylmethyl)-1H-indazole-5-carboxamide hydrochloride (29.8 mg, 100%).

Workup

  1. stirringthe resulting mixture was stirred
  2. temperaturewhile being maintained at room temperature
  3. filtrationThen, the resulting slurry was collected by filtration
  4. customdried under reduced pressure
  5. stirringthe resulting crude product residue was stirred in methanol (3.0 ml) for 1 hour
  6. temperaturewith heating
  7. temperatureunder reflux
  8. temperaturewhile maintaining the temperature
  9. concentrationThe resulting mixture was concentrated to dryness

Sources & evidence

ORD record
ord-3aee8ef091314cd880c46e3be61a6b87
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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