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

HRID 12831

Reaktionsgleichung

Reaktionsgleichung von HRID 12831
[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

Komponenten

8

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-00ba1c16f1b0406f8ac1ff0d65001f8a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728029B2

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