2-Aminoadamantane hydrochloride → 1-tert-butyl-5-chloro-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

HRID 12858

반응식

HRID 12858 반응식
[C:1]([N:5]1[C:9]([Cl:10])=[C:8]([C:11]([OH:13])=O)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.Cl.[CH:44]12[CH2:53][CH:48]3[CH2:49][CH:50]([CH2:52][CH:46]([CH2:47]3)[CH:45]1[NH2:54])[CH2:51]2>CN(C)C=O.C(Cl)Cl>[CH:44]12[CH2:53][CH:48]3[CH2:49][CH:50]([CH2:52][CH:46]([CH2:47]3)[CH:45]1[NH:54][C:11]([C:8]1[CH:7]=[N:6][N:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:9]=1[Cl:10])=[O:13])[CH2:51]2

참가 물질

6

반응물 4

HCID 253312-Aminoadamantane hydrochlorideHCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 534235531-(tert-Butyl)-5-chloro-1H-pyrazole-4-carboxylic acid

생성물 1

HCID 250144171-tert-butyl-5-chloro-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide수율 80%

시약·촉매·용매 1

HCID 22350042dichloromethane N,N-dimethylformamide용매

실험 절차

To a stirred solution of 1-tert-butyl-5-chloro-1H-pyrazole-4-carboxylic acid (3.040 g; 15.0 mmol) in N,N-dimethylformamide/methylene chloride (1:4 ratio, 20 mL) at room temperature was added diisopropylethylamine (21.2 mL; 120.4 mmol). TSTU (5.420 g; 18.0 mmol) was then added. The resulting mixture was allowed to stir at room temp. for 2 hr and then 2-adamantylamine hydrochloride (2.844 g; 15.0 mmol) was added. The mixture was allowed to stir over the weekend at room temperature and then concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The resulting light yellow gum was triturated with diethyl ether to provide 1-tert-butyl-5-chloro-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (4.02 g, 80%) as a white powder.

후처리

  1. stirringto stir over the weekend at room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting light yellow gum was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-32b0a4940c424d8aa6d1a6599c794229
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728029B2

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