Aminoisobutyric acid → 5-Isopropylamino-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

HRID 12847

Reaction equation

HRID 12847 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.[NH2:28][C:29](C)([CH3:33])[C:30](O)=O>>[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:28][CH:29]([CH3:33])[CH3:30])=[O:13])[CH2:8]2

Participants

4

Reactant 3

HCID 6119Aminoisobutyric acidHCID 8471TriethylamineHCID 250135435-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

Product 1

HCID 250133785-Isopropylamino-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), triethylamine (0.43 mL; 3.1 mmol) and 2-aminoisobutyric acid (320 mg; 3.1 mmol) under microwave irradiation for 6 hr according to the procedure described for Example 14 provided after purification by reverse phase HPLC, 5-isopropylamino-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (28 mg, 29%) as an off-white powder. ES-HRMS m/e calcd for C18H29N4O (M+H+) 317.2336, found 317.2334.

Workup

  1. temperatureHeating
  2. customunder microwave irradiation for 6 hr
  3. customprovided
  4. customafter purification by reverse phase HPLC, 5-isopropylamino-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (28 mg, 29%) as an off-white powder

Sources & evidence

ORD record
ord-998eec4678a34453b962037b0f34f3c6
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Linked notes

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