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

HRID 12832

反応式

HRID 12832 の反応式
[C:1]([N:5]1[C:9]([C:10]([F:13])([F:12])[F:11])=[C:8]([C:14]([OH:16])=O)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.Cl.[NH2:47][CH:48]1[CH:55]2[CH2:56][CH:51]3[CH2:52][CH:53]([CH2:57][CH:49]1[CH2:50]3)[CH2:54]2>ClCCl.CN(C=O)C.O>[CH:49]12[CH2:57][CH:53]3[CH2:52][CH:51]([CH2:56][CH:55]([CH2:54]3)[CH:48]1[NH:47][C:14]([C:8]1[CH:7]=[N:6][N:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:9]=1[C:10]([F:11])([F:12])[F:13])=[O:16])[CH2:50]2

参加物

8

反応物 4

HCID 253312-Aminoadamantane hydrochlorideHCID 81531DiisopropylethylamineHCID 14820391-tert-Butyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid2 回HCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate

生成物 1

HCID 250135441-tert-butyl-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

tert-Butyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (Intermediate 7, 61 mg, 0.26 mmol) was dissolved in a mixture of dry dichloromethane (3.2 mL) and dry DMF (0.8 mL). DIPEA (0.23 mL, 1.3 mmol) and TSTU (93 mg, 0.28 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 (58 mg, 0.31 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 C-18 reversed phase HPLC with a gradient of 10-100% acetonitrile/water to give 1-tert-butyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (62 mg, 65%). Mass spectrum: m/z: 370.2 (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 C-18

出典と根拠

ORDレコード
ord-d53e24288b474cab86af0923b73f4cca
出典データセット
uspto-grants-2010_06
特許番号
US07728029B2

関連ノート

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