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2-Aminoadamantane hydrochloride → 5-chloro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

HRID 12834
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 12834
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[C:9]([OH:11])=O.CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.Cl.[NH2:42][CH:43]1[CH:50]2[CH2:51][CH:46]3[CH2:47][CH:48]([CH2:52][CH:44]1[CH2:45]3)[CH2:49]2>ClCCl.CN(C=O)C.O>[CH:44]12[CH2:52][CH:48]3[CH2:47][CH:46]([CH2:51][CH:50]([CH2:49]3)[CH:43]1[NH:42][C:9]([C:3]1[C:4]([CH3:8])=[N:5][N:6]([CH3:7])[C:2]=1[Cl:1])=[O:11])[CH2:45]2
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Komponenten

8

Edukt 4

HCID 253312-Aminoadamantane hydrochlorideHCID 81531DiisopropylethylamineHCID 27796525-chloro-1,3-dimethyl-1H-pyrazole-4-carboxylic acidHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate

Produkt 1

HCID 250135475-chloro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamideAusbeute 58,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid (69 mg, 0.4 mmol, CAS#: 27006-82-2, purchased from Maybridge) 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, 0.4 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-1,3-dimethyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (72 mg, 58%). Mass spectrum: m/z: 308.1 (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-50e7ad3ab4024b1b8b9a373a9da549ff
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07728029B2

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