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Ethyl Acetate → 4-{6-Amino-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-3-yl}-piperidine-1-carboxamide

HRID 911999
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 911999
[NH2:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([C:11]3[CH2:12][CH2:13][N:14]([C:17]([NH2:19])=[O:18])[CH2:15][CH:16]=3)=[CH:9][O:10][C:4]=2[C:3]=1[O:20][C@@H:21]([C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[C:25]([F:30])[C:24]=1[Cl:31])[CH3:22].CCOC(C)=O>[Pd].CO>[NH2:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([CH:11]3[CH2:12][CH2:13][N:14]([C:17]([NH2:19])=[O:18])[CH2:15][CH2:16]3)=[CH:9][O:10][C:4]=2[C:3]=1[O:20][C@@H:21]([C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[C:25]([F:30])[C:24]=1[Cl:31])[CH3:22]
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Komponenten

5

Edukt 2

HCID 8857Ethyl AcetateHCID 441816544-{6-Amino-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-furo[3,2-c]pyridin-3-yl}-3,6-dihydro-2H-pyridine-1-carboxamide

Produkt 1

HCID 578123434-{6-Amino-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-3-yl}-piperidine-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator
HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

A mixture of 4-{6-amino-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridine-3-yl}-3,6-dihydro-2H-pyridine-1-carboxamide (17.0 mg, 0.037 mmol), palladium 10% wt on activated carbon (10 mg), EtOAc (4 mL) and MeOH (0.4 mL) was flushed with nitrogen, then a hydrogen (0.5 L) balloon was added, and the mixture was stirred at rt for 3 h. The suspension was filtered through a syringe filter pad, and the filtrate was concentrated in vacuo. The material was redissolved in MeOH (0.5 mL) and purified via HPLC. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ=1.55-1.69 (m, 2H), 1.87 (d, J=6.8 Hz, 3H), 1.98-2.06 (m, 2H), 2.89-3.03 (m, 3H), 4.11 (d, J=12.9 Hz, 2H), 6.53 (q, J=6.7 Hz, 1H), 7.18-7.25 (m, 1H), 7.37-7.43 (m, 2H), 8.02 (s, 1H). MS (ES+): m/z 467.01/469.00 (100/69) [MH+]. HPLC: tR=2.58 min (ZQ3, polar—5 min).

Aufarbeitung

  1. customwas flushed with nitrogen
  2. additiona hydrogen (0.5 L) balloon was added
  3. filtrationThe suspension was filtered through a syringe
  4. filtrationfilter pad
  5. concentrationthe filtrate was concentrated in vacuo
  6. dissolutionThe material was redissolved in MeOH (0.5 mL)
  7. custompurified via HPLC
  8. additionThe fractions containing the pure product
  9. concentrationwere concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-77baab77cd8141dea17bb0193e0e7260
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08022206B2

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