Ethanolamine → 5-(2-Hydroxy-ethylamino)-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

HRID 12838

Reaction equation

HRID 12838 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.[CH2:21]([CH2:23][NH2:24])[OH:22]>>[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[NH:24][CH2:23][CH2:21][OH:22])=[O:13])[CH2:8]2

Participants

3

Reactant 2

HCID 700EthanolamineHCID 250135435-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

Product 1

HCID 250138595-(2-Hydroxy-ethylamino)-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, 59 mg; 0.20 mmol) and ethanolamine (0.20 mL; 3.3 mmol) under microwave irradiation according to the procedure described in Example 14 Step 2 provided after purification by reverse phase HPLC, 5-(2-hydroxy-ethylamino)-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (26 mg, 41%) as a white powder. ES-HRMS m/e calcd for C17H27N4O2 (M+H+) 319.2129, found 319.2127.

Workup

  1. temperatureHeating
  2. customunder microwave irradiation
  3. customprovided
  4. customafter purification by reverse phase HPLC, 5-(2-hydroxy-ethylamino)-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (26 mg, 41%) as a white powder

Sources & evidence

ORD record
ord-30b533f8974244a4b07fda87e628beb1
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Linked notes

Loading…