3-Aminopyridine → HCID 44235024, Verbindung

HRID 1093852Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1093852
CCN(C(C)C)C(C)C.[N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]2[CH:20]=[C:19]([C:21]([NH:23][CH2:24][C:25]([OH:27])=O)=[O:22])[N:18]=[N:17]2)[CH:11]=1.NC1C=NC=CC=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[F:57][C:58]1[CH:69]=[CH:68][C:67]([F:70])=[CH:66][C:59]=1[O:60][CH:61]1[CH2:65][CH2:64][NH:63][CH2:62]1>CN(C=O)C.O>[F:57][C:58]1[CH:69]=[CH:68][C:67]([F:70])=[CH:66][C:59]=1[O:60][CH:61]1[CH2:65][CH2:64][N:63]([C:25](=[O:27])[CH2:24][NH:23][C:21]([C:19]2[N:18]=[N:17][N:16]([C:12]3[CH:11]=[N:10][CH:15]=[CH:14][CH:13]=3)[CH:20]=2)=[O:22])[CH2:62]1

Komponenten

9

Edukt 6

HCID 100093-AminopyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 450755433-(2,5-Difluorophenoxy)pyrrolidine--hydrogen chloride (1/1)HCID 66592012[(1-pyridin-3-yl-1H-[1,2,3]triazole-4-carbonyl)-amino]-acetic acid

Produkt 1

HCID 44235024HCID 44235024, VerbindungAusbeute 37,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIPEA (156.8 mg, 1.2 mmol) was added to a stirred solution of [(1-pyridin-3-yl-1H-[1,2,3]triazole-4-carbonyl)-amino]-acetic acid (prepared by the method used for the synthesis of Intermediate 64, starting from 3-aminopyridine, and subsequently, application of Step 3 of the General Scheme) (75 mg, 0.3 mmol) in DMF (3 mL) followed by HOBt (45 mg, 0.33 mmol) and EDCI (116 mg, 0.6 mmol). After 2 minutes of stirring, 3-(2,5-difluoro-phenoxy)-pyrrolidine hydrochloride (prepared by the method used for the synthesis of Intermediate 72) (71.5 mg, 0.3 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and precipitate was collected to afford 48 mg (37.2% Yield) of 1-pyridin-3-yl-1H-[1,2,3]triazole-4-carboxylic acid {2-[3-(2,5-difluoro-phenoxy)-pyrrolidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 429.14, 92.32%. 1H NMR (300 MHz, DMSO-d6): δ 9.5 (s, 1H), 9.2 (d, 1H), 8.75 (d, 1H), 8.6 (m, 1H), 8.4 (m, 1H), 7.7 (q, 1H), 7.3-7.2 (m, 2H), 6.9-6.7 (m, 1H), 5.3-5.1 (d, 1H), 4.25-4.1 (m, 2H), 4.0-3.5 (m, 4H), 2.3-2.2 (m, 1H), 2.2-2.05 (m, 1H).

Aufarbeitung

  1. customprepared by the method
  2. additionwas added
  3. stirringthe resulting mixture was stirred at room temperature overnight
  4. customprecipitate was collected

Quellen und Nachweise

ORD-Eintrag
ord-cebdae12fd7d4037a33d81fd5d84f948
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129376B2

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