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

HRID 12831

反応式

HRID 12831 の反応式
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]([OH:10])=O.CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.Cl.[NH2:41][CH:42]1[CH:49]2[CH2:50][CH:45]3[CH2:46][CH:47]([CH2:51][CH:43]1[CH2:44]3)[CH2:48]2>ClCCl.CN(C=O)C.O>[CH:43]12[CH2:51][CH:47]3[CH2:46][CH:45]([CH2:50][CH:49]([CH2:48]3)[CH:42]1[NH:41][C:8]([C:3]1[CH:4]=[N:5][N:6]([CH3:7])[C:2]=1[Cl:1])=[O:10])[CH2:44]2

参加物

8

反応物 4

HCID 253312-Aminoadamantane hydrochlorideHCID 81531DiisopropylethylamineHCID 27357745-Chloro-1-methyl-1H-pyrazole-4-carboxylic acidHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate

生成物 1

HCID 250135435-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide収率 60%

試薬・触媒・溶媒 3

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

実験手順

5-Chloro-1-methyl-1H-pyrazole-4-carboxylic acid (64 mg, 0.4 mmol, CAS#: 54367-66-7, purchased from Oakwood) 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 5-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (70 mg, 60%). Mass spectrum: m/z: 294.1 (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-00ba1c16f1b0406f8ac1ff0d65001f8a
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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