Butyric acid, 4-piperidino- → N-[5-(4-Methoxy-phenyl)-2H-pyrazol-3-yl]-4-piperidin-1-yl-butyramide

HRID 1695215Notes

Reaction equation

HRID 1695215 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:13][C:14]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[NH:16][N:15]=1>>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([C:17]2[CH:18]=[C:14]([NH:13][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[NH:15][N:16]=2)=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 20794Butyric acid, 4-piperidino-HCID 27564693-Amino-5-(4-methoxyphenyl)pyrazole

Product 1

HCID 178488667N-[5-(4-Methoxy-phenyl)-2H-pyrazol-3-yl]-4-piperidin-1-yl-butyramide

Procedure

To a suspension of 4-piperidin-1-yl-butyric acid (1.32 g, 7.93 mmol) in 12,2-dichloroethane (20 mL), N,N′-carbonyldiimidazole (1.2 g, 7.4 mmol) was added and the mixture was stirred at room temperature for 2 hours (when all the aminoacid was activated complete dissolution of the suspension was generally observed). 3-Amino-5-(4-methoxyphenyl)pyrazole (1 g, 5.29 mmol) was then added and the reaction was stirred for further 10 hours. Upon reaction completion (as monitored by LC-MS) the formation of two isomers was observed, and the mixture was heated at 50° C. until the conversion of the less stable isomer to the title compound was observed (as monitored by LC-MS). The solvent was washed with sat. Na2CO3 solution, extracted and removed under reduced pressure. The crude was crystallised from acetonitrile to give 1.2 g of the title compound (Yield: 70%).

Workup

  1. additionwas added
  2. dissolutioncomplete dissolution of the suspension
  3. customUpon reaction completion (as monitored by LC-MS) the formation of two isomers

Sources & evidence

ORD record
ord-2a92577831104d1aa78fbb0684a022c5
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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