Triethylamine → Methyl-5-[1,2,4]triazol-1-yl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

HRID 12839

Reaction equation

HRID 12839 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.C(N(CC)CC)C.[NH:28]1[CH:32]=[N:31][CH:30]=[N:29]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]([CH3:20])[C:18]=1[N:28]1[CH:32]=[N:31][CH:30]=[N:29]1)=[O:13])[CH2:8]2

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 92571H-1,2,4-TriazoleHCID 250135435-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

Product 1

HCID 25013860Methyl-5-[1,2,4]triazol-1-yl-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), triethylamine (0.22 mL; 1.56 mmol) and 1,2,4-triazole (0.21 g; 3.0 mmol) under microwave irradiation for 4 hr according to the procedure described for Example 14 provided after purification by reverse phase HPLC, 1-methyl-5-[1,2,4]triazol-1-yl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (11 mg, 11%) as an off-white powder. ES-HRMS m/e calcd for C17H22N6O (M+H+) 327.1928, found 327.1924.

Workup

  1. temperatureHeating
  2. customunder microwave irradiation for 4 hr
  3. customprovided
  4. customafter purification by reverse phase HPLC, 1-methyl-5-[1,2,4]triazol-1-yl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (11 mg, 11%) as an off-white powder

Sources & evidence

ORD record
ord-f0bf1e0f3d224daa902dc6a617147a16
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Linked notes

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