Pyrazole → 2'-tert-butyl-2'H-[1,3']bipyrazolyl-4'-carboxylic acid adamantan-2-ylamide

HRID 12853

반응식

HRID 12853 반응식
[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]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1Cl)=[O:13])[CH2:8]2.[NH:24]1[CH:28]=[CH:27][CH:26]=[N:25]1.[F-].[K+]>CS(C)=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]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1[N:24]1[CH:28]=[CH:27][CH:26]=[N:25]1)=[O:13])[CH2:8]2

참가 물질

5

반응물 3

HCID 1048PyrazoleHCID 522689Potassium FluorideHCID 250144171-tert-butyl-5-chloro-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

생성물 1

HCID 167425402'-tert-butyl-2'H-[1,3']bipyrazolyl-4'-carboxylic acid adamantan-2-ylamide수율 41%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

In a Personal Chemistry microwave process tube (Biotage AB, Sweden), 1-tert-butyl-5-chloro-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (Example 36, 100 mg, 0.30 mmol), pyrazole (41 mg, 0.60 mmol), KF (35 mg, 0.60 mmol) and DMSO (2 mL) were well mixed. The tube was sealed with a septum and was submitted to 150 W microwave irradiation using a Personal Chemistry Microwave Synthesis system (Biotage AB, Sweden) at 230° C. for 20 minutes. The reaction mixture was partitioned between ethyl acetate and water and the aqueous phase was extracted three times with ethyl acetate. The organic phases were combined, concentrated in vacuo and purified by C-18 reversed phase prep-HPLC with a gradient of 10-100% acetonitrile/water to give 2′-tert-butyl-2′H-[1,3′]bipyrazolyl-4′-carboxylic acid adamantan-2-ylamide (45 mg, 41%). Mass spectrum: m/z: 368.2 (M+1).

후처리

  1. customThe tube was sealed with a septum
  2. customwas submitted to 150 W microwave irradiation
  3. customa Personal Chemistry Microwave Synthesis system (Biotage AB, Sweden) at 230° C. for 20 minutes
  4. customThe reaction mixture was partitioned between ethyl acetate and water
  5. extractionthe aqueous phase was extracted three times with ethyl acetate
  6. concentrationconcentrated in vacuo
  7. custompurified by C-18

출처 및 근거

ORD 기록
ord-c38d0564c8994c85877cb4441405fdcf
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728029B2

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