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2-Aminoadamantane hydrochloride → 1-methyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

HRID 12830
ノート
印刷プレビュー

反応式

HRID 12830 の反応式
[CH3:1][N:2]1[C:6]([C:7]([F:10])([F:9])[F:8])=[C:5]([C:11]([OH:13])=O)[CH:4]=[N:3]1.CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.Cl.[NH2:44][CH:45]1[CH:52]2[CH2:53][CH:48]3[CH2:49][CH:50]([CH2:54][CH:46]1[CH2:47]3)[CH2:51]2>ClCCl.CN(C=O)C.O>[CH:46]12[CH2:54][CH:50]3[CH2:49][CH:48]([CH2:53][CH:52]([CH2:51]3)[CH:45]1[NH:44][C:11]([C:5]1[CH:4]=[N:3][N:2]([CH3:1])[C:6]=1[C:7]([F:10])([F:9])[F:8])=[O:13])[CH2:47]2
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 253312-Aminoadamantane hydrochlorideHCID 81531DiisopropylethylamineHCID 28077711-Methyl-5-(trifluoromethyl)pyrazole-4-carboxylic AcidHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate

生成物 1

HCID 250135421-methyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide収率 65%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

Methyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (77 mg, 0.4 mmol, CAS#: 119083-00-0, purchased from Bionet) was dissolved in a mixture of dry dichloromethane (3.2 mL) and dry DMF (0.8 mL). DIPEA (0.28 mL, 1.6 mmol) and TSTU (145 mg, 0.44 mmol) were added to the above mixture. After the mixture was stirred for 1 h, the appearance of active ester was detected by LC-MS. Then 2-aminoadamantane hydrochloride (75 mg, 0.4 mmol) was added. After another 2 hours water was added and the organic layer was separated. The aqueous layer was extracted twice with dichloromethane. The combined organic phases were dried under vacuum and purified by C-18 reversed phase HPLC with a gradient of 10-100% acetonitrile/water to give 1-methyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (85 mg, 65%). Mass spectrum: m/z: 328.2 (M+1).

後処理

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted twice with dichloromethane
  3. customThe combined organic phases were dried under vacuum
  4. custompurified by C-18

出典と根拠

ORDレコード
ord-b7c63b53a9564e1ea614af812d6e8e45
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07728029B2

反応ノート

読み込み中…

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