2-Aminoadamantane hydrochloride → N-(2-adamantyl)-1-(4-chloro-2-methyl-phenyl)-5-tert-butyl-pyrazole-4-carboxamide

HRID 1160559노트

반응식

HRID 1160559 반응식
Cl.CN(C)CCCN=C=NCC.Cl.[CH:14]12[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH:15]1[NH2:24])[CH2:21]2.[C:25]([C:29]1[N:33]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:35]=2[CH3:41])[N:32]=[CH:31][C:30]=1[C:42](O)=[O:43])([CH3:28])([CH3:27])[CH3:26].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>CN(C=O)C.CCOCC>[CH:14]12[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH:15]1[NH:24][C:42]([C:30]1[CH:31]=[N:32][N:33]([C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:35]=3[CH3:41])[C:29]=1[C:25]([CH3:28])([CH3:27])[CH3:26])=[O:43])[CH2:21]2

참가 물질

8

반응물 5

HCID 253312-Aminoadamantane hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 595160855-tert-butyl-1-(4-chloro-2-methylphenyl)-1H-pyrazole-4-carboxylic acid

생성물 1

HCID 59516130N-(2-adamantyl)-1-(4-chloro-2-methyl-phenyl)-5-tert-butyl-pyrazole-4-carboxamide수율 90.1%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

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온도
20 °C

실험 절차

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (Intermediate#115) (515 mg, 2.68 mmol) was added in one portion to 2-Adamantanamine hydrochloride (420 mg, 2.24 mmol), 5-tert-butyl-1-(4-chloro-2-methylphenyl)-1H-pyrazole-4-carboxylic acid (655 mg, 2.24 mmol), 1-Hydroxybenzotriazole (363 mg, 2.68 mmol) and N-Ethyldiisopropylamine (1.149 mL, 6.71 mmol) in DMF (10 mL). The resulting mixture was stirred at 20° C. for 18 hours. The reaction mixture was diluted with Et2O (100 mL), and washed sequentially with water (3×25 mL), and saturated brine (25 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford desired product N-(2-adamantyl)-1-(4-chloro-2-methyl-phenyl)-5-tert-butyl-pyrazole-4-carboxamide (860 mg, 90%).

후처리

  1. washwashed sequentially with water (3×25 mL), and saturated brine (25 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated

출처 및 근거

ORD 기록
ord-aaa2ba55859a40fa98eef364871ee868
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816391B2

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