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

HRID 12835
ノート
印刷プレビュー

反応式

HRID 12835 の反応式
[CH:1]1([N:4]2[C:8]([C:9]([F:12])([F:11])[F:10])=[C:7]([C:13]([OH:15])=O)[CH:6]=[N:5]2)[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.Cl.[NH2:46][CH:47]1[CH:54]2[CH2:55][CH:50]3[CH2:51][CH:52]([CH2:56][CH:48]1[CH2:49]3)[CH2:53]2>ClCCl.CN(C=O)C.O>[CH:48]12[CH2:56][CH:52]3[CH2:51][CH:50]([CH2:55][CH:54]([CH2:53]3)[CH:47]1[NH:46][C:13]([C:7]1[CH:6]=[N:5][N:4]([CH:1]3[CH2:2][CH2:3]3)[C:8]=1[C:9]([F:10])([F:11])[F:12])=[O:15])[CH2:49]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 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 589728211-cyclopropyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid2 回

生成物 1

HCID 250135481-cyclopropyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide
収率 56.6%

試薬・触媒・溶媒 3

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

実験手順

1-Cyclopropyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (Intermediate 6, 20 mg, 0.09 mmol) was dissolved in a mixture of dry dichloromethane (1.6 mL) and dry DMF (0.2 mL). DIPEA (0.1 mL, 0.57 mmol) and TSTU (33 mg, 0.11 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 (17 mg, 0.09 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 layers were dried under vacuum and purified by silica chromatography eluting with a gradient of 0-40% ethyl acetate/hexanes, then 40% ethyl acetate/hexanes to give 1-cyclopropyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (18 mg, 56%). Mass spectrum: m/z: 354.2 (M+1).

後処理

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted twice with dichloromethane
  3. customThe combined organic layers were dried under vacuum
  4. custompurified by silica chromatography
  5. washeluting with a gradient of 0-40% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-4f6a0d022ce842589a91c7fec504bf5e
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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