StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Dimethylformamide → (2S,4S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-(benzylamino)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

HRID 1630283
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1630283
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:9]1([CH2:14][C:15]([N:17]2[CH2:21][C@@H:20]([NH2:22])[CH2:19][C@H:18]2[C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)=[CH:28][CH:27]=2)=[O:24])=[O:16])[CH:13]=[N:12][CH:11]=[N:10]1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>Cl>[N:9]1([CH2:14][C:15]([N:17]2[CH2:21][C@@H:20]([NH:22][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:19][C@H:18]2[C:23]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([O:32][C:33]3[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=3)=[CH:30][CH:31]=2)=[O:24])=[O:16])[CH:13]=[N:12][CH:11]=[N:10]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67009874HCID 67009874, Verbindung

Produkt 1

HCID 45377581(2S,4S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-(benzylamino)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideAusbeute 22,3 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

Step (b) Benzyl bromide (0.131 mL, 1.10 mmol) was added to a flask charged with (2S,4S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-amino-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (0.465 g, 1.10 mmol), DMF (10 mL), and K2CO3 (0.607 g, 4.40 mmol). The reaction mixture was stirred at ambient temperature for 30 minutes and then diluted with 1N hydrochloric acid (30 mL). The dilution was washed with ethyl acetate (30 mL). The aqueous layer was basified with 2N sodium hydroxide (40 mL) and then extracted with methylene chloride (40 mL). The extract was washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated. Product was purified from the residue by reverse phase HPLC to give Compound 80, (2S,4S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-(benzylamino)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (126 mg, 0.245 mmol, 22%), as an off-white solid. 1H-NMR (400 MHz, CDCl3): 12.08 (br. s, 1H), 11.13 (s, 1H), 9.05 (s, 1H), 8.24-8.16 (m, 1H), 7.99-7.94 (m, 1H), 7.41-7.20 (m, 4H), 7.04-6.82 (m, 7H), 5.21 (d, J=16.0 Hz, 1H), 5.00 (s, 1H), 4.93 (d, J=16.0 Hz, 1H), 4.74-4.57 (m, 1H), 3.96-5.59 (m, 3H), 3.14-3.07 (m, 2H), 2.62-2.00 (m, 2H). MS (EI) for C28H27FN6O3. found 515.2 (MH+).

Aufarbeitung

  1. washThe dilution was washed with ethyl acetate (30 mL)
  2. extractionextracted with methylene chloride (40 mL)
  3. washThe extract was washed with brine (20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customProduct was purified from the residue by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-13a78c7b6ab1442780a1f3ff463beae3
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08791102B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion