4-Piperidinecarboxylic acid → HCID 16066664, compound

HRID 1896202Notes

Reaction equation

HRID 1896202 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:18][C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=2)[C:5]2[N:10]([CH2:11][CH2:12][O:13][CH2:14][CH3:15])[N:9]=[C:8]([CH2:16][CH3:17])[C:6]=2[N:7]=1.[NH:26]1[CH2:34][CH2:33][CH:29]([C:30]([OH:32])=[O:31])[CH2:28][CH2:27]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>O.CN(C)C=O.CS(C)=O>[CH2:14]([O:13][CH2:12][CH2:11][N:10]1[C:5]2[C:4]([NH:18][C:19]3[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=3)=[N:3][C:2]([N:26]3[CH2:34][CH2:33][CH:29]([C:30]([OH:32])=[O:31])[CH2:28][CH2:27]3)=[N:7][C:6]=2[C:8]([CH2:16][CH3:17])=[N:9]1)[CH3:15]

Participants

9

Reactant 5

HCID 37734-Piperidinecarboxylic acidHCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 16222003HCID 16222003, compound

Product 1

HCID 16066664HCID 16066664, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
112.5 °C

Procedure

Alternatively, a mixture of N-[5-chloro-1-(2-ethoxyethyl)-3-ethyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl]-4-methylpyridin-2-ylamine from step 5 can be combined with isonipecotic acid (between 1 to 10 equivalents) and a base and heated between 100-125° C. in a solvent until the reaction is complete. Suitable bases include cesium carbonate, sodium carbonate and potassium carbonate. Suitable solvents include DMSO and N,N-dimethylformamide. Upon cooling, water can be added and the basic solution extracted (between 1 to 3 times) with an organic solvent such as ethyl acetate. The remaining basic layer is acidified to pH 5 with HCl. The mixture is stirred for approximately 1 hour. The solid is filtered off, washed with water, and dried in vaccuo to provide the title compound.

Workup

  1. temperatureUpon cooling
  2. extractionthe basic solution extracted (between 1 to 3 times) with an organic solvent such as ethyl acetate
  3. filtrationThe solid is filtered off
  4. washwashed with water
  5. customdried in vaccuo

Sources & evidence

ORD record
ord-7606447d75794ba0aec0f13738bc4a86
Source dataset
uspto-grants-2013_08
Patent number
US08518956B2

Reaction notes

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