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Benzyl 3-(1-carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-fluorophenylcarbamate → 4-(3-amino-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamide

HRID 2361339
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2361339
[C:1]([C:4]1[C:9]2[NH:10][C:11]3[C:16]([C:8]=2[C:7]([C:22]2[C:23]([F:39])=[C:24]([NH:28]C(=O)OCC4C=CC=CC=4)[CH:25]=[CH:26][CH:27]=2)=[CH:6][N:5]=1)=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][O:20][CH3:21])[CH:12]=3)(=[O:3])[NH2:2]>C1COCC1.CO.[Pd]>[NH2:28][C:24]1[C:23]([F:39])=[C:22]([C:7]2[C:8]3[C:16]4[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:14][CH:15]=4)[NH:10][C:9]=3[C:4]([C:1]([NH2:2])=[O:3])=[N:5][CH:6]=2)[CH:27]=[CH:26][CH:25]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 1

HCID 67994974Benzyl 3-(1-carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-fluorophenylcarbamate

Produkt 1

HCID 679950434-(3-amino-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamideAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

A solution of benzyl 3-(1-carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-fluorophenylcarbamate (0.6318 g, 1.195 mmol) and 10% Pd/C (0.191 g, 0.179 mmol) in THF (31.9 mL) and MeOH (47.8 mL) was hydrogenated. After 2 hr, the reaction was filtered through a wad of CELITE® and rinsed with THF and MeOH. The filtrate was concentrated in vacuo, dissolved in EtOAc (100 mL) and brine (25 mL). The layers were separated, and the aqueous layer was extracted with EtOAc (50 mL). The organic layers were combined, dried over MgSO4, and concentrated in vacuo to give the desired product (0.4462 g, 1.007 mmol, 84% yield) as a tan solid.

Aufarbeitung

  1. filtrationthe reaction was filtered through a wad of CELITE®
  2. washrinsed with THF and MeOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutiondissolved in EtOAc (100 mL)
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with EtOAc (50 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5683d978f80c432a80ddb2a767b0794d
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08685969B2

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