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

HRID 12858

反応式

HRID 12858 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 22350042dichloromethane N,N-dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-32b0a4940c424d8aa6d1a6599c794229
出典データセット
uspto-grants-2010_06
特許番号
US07728029B2

関連ノート

読み込み中…