Diethylamine → 5-Diethylamino-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

HRID 12850Notes

Reaction equation

HRID 12850 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.[CH2:21]([NH:23][CH2:24][CH3:25])[CH3:22]>>[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:23]([CH2:24][CH3:25])[CH2:21][CH3:22])=[O:13])[CH2:8]2

Participants

3

Reactant 2

HCID 8021DiethylamineHCID 250135435-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

Product 1

HCID 250142485-Diethylamino-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 diethylamine (0.32 mL; 3.1 mmol) under microwave irradiation according to the procedure described for Example 14 provided after purification by reverse phase HPLC, 5-diethylamino-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (16 mg, 16%) as an off-white powder. ES-MS m/e calcd for C19H31N4O (M+H+) 331, found 331.

Workup

  1. temperatureHeating
  2. customunder microwave irradiation
  3. customprovided
  4. customafter purification by reverse phase HPLC, 5-diethylamino-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (16 mg, 16%) as an off-white powder

Sources & evidence

ORD record
ord-deb484043d9b43fdb95c008e96681372
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Reaction notes

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