1-Benzylpiperazine → HCID 25014246, compound

HRID 12849Notes

Reaction equation

HRID 12849 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]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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:31]1[CH2:32][CH2:33][N:28]([CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:29][CH2:30]1)=[O:13])[CH2:8]2

Participants

3

Reactant 2

HCID 759941-BenzylpiperazineHCID 250135435-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

Product 1

HCID 25014246HCID 25014246, compound

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 N-benzylpiperazine (0.54 mL; 3.1 mmol) under microwave irradiation according to the procedure described for Example 14 provided after purification by reverse phase HPLC, 5-(4-benzyl-piperazin-1-yl)-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (50 mg, 38%) as an off-white powder. ES-HRMS m/e calcd for C26H35N5O (M+H+) 434.2915, found 434.2910.

Workup

  1. temperatureHeating
  2. customunder microwave irradiation
  3. customprovided
  4. customafter purification by reverse phase HPLC, 5-(4-benzyl-piperazin-1-yl)-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (50 mg, 38%) as an off-white powder

Sources & evidence

ORD record
ord-fb5372af97f04492ba6f9addca094f77
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Reaction notes

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