Pyrrolidine → tert-Butyl-5-pyrrolidin-1-yl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

HRID 12851

Reaction equation

HRID 12851 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[CH2:28][CH2:27][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[CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:13])[CH2:8]2

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 250144171-tert-butyl-5-chloro-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

Product 1

HCID 25014249tert-Butyl-5-pyrrolidin-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 (100 mg; 0.30 mmol) and pyrrolidine (0.25 mL; 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-piperidin-1-yl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (14 mg, 16%) as an white solid. ES-HRMS m/e calcd for C22H34N4O (M+H+) 371.2806, found 371.2801.

Workup

  1. temperatureHeating
  2. customunder microwave irradiation
  3. customprovided
  4. customafter purification by reverse phase HPLC, 1-tert-butyl-5-piperidin-1-yl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (14 mg, 16%) as an white solid

Sources & evidence

ORD record
ord-1a91fb6fdb434107a50d6b21eddb5fad
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Linked notes

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