Piperidin-4-ol → 5-(4-Hydroxy-piperidin-1-yl)-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

HRID 12842

Reaction equation

HRID 12842 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([C:14]1[CH:15]=[N:16][N:17]([CH3:20])[C:18]=1Cl)=[O:13])[CH2:8]2.[OH:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([C:14]1[CH:15]=[N:16][N:17]([CH3:20])[C:18]=1[N:25]1[CH2:26][CH2:27][CH:22]([OH:21])[CH2:23][CH2:24]1)=[O:13])[CH2:8]2

Participants

3

Reactant 2

HCID 79341Piperidin-4-olHCID 250135435-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

Product 1

HCID 250140405-(4-Hydroxy-piperidin-1-yl)-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

Procedure

Heating a mixture of 5-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (Example 5, 88 mg; 0.30 mmol) and 4-hydroxypiperidine (0.31 mL; 3.0 mmol) under microwave irradiation according to the procedure described for Example 14 provided after purification by reverse phase HPLC, 5-(4-hydroxy-piperidin-1-yl)-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (87 mg, 81%) as an off-white powder. ES-HRMS m/e calcd for C20H31N4O2 (M+H+) 359.2442, found 359.2437.

Workup

  1. temperatureHeating
  2. customunder microwave irradiation
  3. customprovided
  4. customafter purification by reverse phase HPLC, 5-(4-hydroxy-piperidin-1-yl)-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (87 mg, 81%) as an off-white powder

Sources & evidence

ORD record
ord-2c40dc5bfbc54c5f8d78a10378e54cac
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Linked notes

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