1-Amino-2-propanol → 5-(2-Hydroxy-propylamino)-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

HRID 12844

Reaction equation

HRID 12844 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.[NH2:21][CH2:22][CH:23]([OH:25])[CH3:24]>>[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:21][CH2:22][CH:23]([OH:25])[CH3:24])=[O:13])[CH2:8]2

Participants

3

Reactant 2

HCID 41-Amino-2-propanolHCID 250135435-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

Product 1

HCID 250140425-(2-Hydroxy-propylamino)-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 1-amino-2-propanol (0.25 mL; 3.0 mmol) under microwave irradiation according to the procedure described for Example 14 provided after purification by reverse phase HPLC, 5-(2-hydroxy-propylamino)-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (65 mg, 65%) as an off-white powder. ES-HRMS m/e calcd for C18H29N4O2 (M+H+) 333.2285, found 333.2282.

Workup

  1. temperatureHeating
  2. customunder microwave irradiation
  3. customprovided
  4. customafter purification by reverse phase HPLC, 5-(2-hydroxy-propylamino)-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (65 mg, 65%) as an off-white powder

Sources & evidence

ORD record
ord-31cb6ba6b59248c988328b6a6d74b4e2
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Linked notes

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