(2-Methoxyethyl)(methyl)amine → 5-[(2-Methoxy-ethyl)-methyl-amino]-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

HRID 12852

Reaction equation

HRID 12852 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][O:22][CH2:23][CH2:24][NH:25][CH3:26]>>[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:25]([CH2:24][CH2:23][O:22][CH3:21])[CH3:26])=[O:13])[CH2:8]2

Participants

3

Reactant 2

HCID 300977(2-Methoxyethyl)(methyl)amineHCID 250135435-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

Product 1

HCID 250142515-[(2-Methoxy-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-methoxy-ethyl)-methyl-amine (276 mg; 3.1 mmol) under microwave irradiation according to the procedure described for Example 14 provided after purification by reverse phase HPLC, 5-[(2-methoxy-ethyl)-methyl-amino]-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (61 mg, 59%) as an off-white powder. ES-HRMS m/e calcd for C19H31N4O2 (M+H+) 347.2442, found 347.2438.

Workup

  1. temperatureHeating
  2. customunder microwave irradiation
  3. customprovided
  4. customafter purification by reverse phase HPLC, 5-[(2-methoxy-ethyl)-methyl-amino]-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (61 mg, 59%) as an off-white powder

Sources & evidence

ORD record
ord-9ce1be243a884eb6b4e2074c4a2c34e8
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Linked notes

Loading…