2-(Methylamino)ethanol → 5-[(2-Hydroxy-ethyl)-methyl-amino]-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

HRID 12843

Reaction equation

HRID 12843 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.[CH3:21][NH:22][CH2:23][CH2:24][OH:25]>>[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:22]([CH2:23][CH2:24][OH:25])[CH3:21])=[O:13])[CH2:8]2

Participants

3

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 250135435-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

Product 1

HCID 250140415-[(2-Hydroxy-ethyl)-methyl-amino]-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 2-(methylamino)ethanol (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-ethyl)-methyl-amino]-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (29 mg, 29%) 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-ethyl)-methyl-amino]-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (29 mg, 29%) as an off-white powder

Sources & evidence

ORD record
ord-c976be99298843fab3c9bf5f89ac994b
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Linked notes

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