Piperidin-4-ol → tert-Butyl-5-(4-hydroxy-piperidin-1-yl)-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

HRID 12860

Reaction equation

HRID 12860 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]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1Cl)=[O:13])[CH2:8]2.[NH:24]1[CH2:29][CH2:28][CH:27]([OH:30])[CH2:26][CH2:25]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]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1[N:24]1[CH2:29][CH2:28][CH:27]([OH:30])[CH2:26][CH2:25]1)=[O:13])[CH2:8]2

Participants

3

Reactant 2

HCID 79341Piperidin-4-olHCID 250144171-tert-butyl-5-chloro-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

Product 1

HCID 25014419tert-Butyl-5-(4-hydroxy-piperidin-1-yl)-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

Procedure

Heating a mixture of 1-tert-butyl-5-chloro-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (Example 36, 101 mg; 0.30 mmol) and piperidin-4-ol (303 mg; 3.0 mmol) under microwave irradiation according to the procedure described in Example 37, Step 5 provided after purification by reverse phase HPLC, 1-tert-butyl-5-(4-hydroxy-piperidin-1-yl)-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (14 mg, 12%) as an off-white powder. ES-HRMS m/e calcd for C23H37N4O2 (M+H+) 357.2649, found 357.2650.

Workup

  1. temperatureHeating
  2. customunder microwave irradiation
  3. customprovided
  4. customafter purification by reverse phase HPLC, 1-tert-butyl-5-(4-hydroxy-piperidin-1-yl)-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (14 mg, 12%) as an off-white powder

Sources & evidence

ORD record
ord-113615d721cf4c3f8fe8c9b69c2ebafd
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Linked notes

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