4-{6-amino-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-3-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester → 7-[(R)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-3-(1,2,3,6-tetrahydropyridin-4-yl)furo[3,2-c]pyridin-6-ylamine

HRID 911956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 911956
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:18]3[CH:19]=[N:20][C:21]([NH2:35])=[C:22]([O:23][C@@H:24]([C:26]4[C:31]([Cl:32])=[CH:30][CH:29]=[C:28]([F:33])[C:27]=4[Cl:34])[CH3:25])[C:17]=3[O:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[Cl:34][C:27]1[C:28]([F:33])=[CH:29][CH:30]=[C:31]([Cl:32])[C:26]=1[C@H:24]([O:23][C:22]1[C:17]2[O:16][CH:15]=[C:14]([C:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=3)[C:18]=2[CH:19]=[N:20][C:21]=1[NH2:35])[CH3:25]

Komponenten

4

Edukt 1

HCID 578125254-{6-amino-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-3-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 578124807-[(R)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-3-(1,2,3,6-tetrahydropyridin-4-yl)furo[3,2-c]pyridin-6-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 4-{6-amino-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-3-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (98.0 mg, 0.188 mmol) in 4 M HCl in 1,4-dioxane (8 mL) was cooled to 0° C., then stirred at 50° C. for 2 h. The material was concentrated in vacuo and then extracted with DCM and sat. aq. NaHCO3. The organic layer was concentrated in vacuo to afford the title compound as a brown solid. 1H NMR (CDCl3, 400 MHz): δ=1.86 (d, J=6.8 Hz, 3H), 2.37-2.47 (m, 2H), 3.15 (t, J=5.8 Hz, 2H), 3.60 (d, J=2.8 Hz, 2H), 4.74 (s, 2H), 6.28 (br, s, 1H), 6.52 (q, J=6.7 Hz, 1H), 7.02-7.08 (m, 1H), 7.27-7.32 (m, 1H), 7.37 (s, 1H), 8.25 (s, 1H). MS (ES+): m/z 422.06 [MH+]. HPLC: tR=2.23 min (ZQ3, polar—5 min).

Aufarbeitung

  1. concentrationThe material was concentrated in vacuo
  2. extractionextracted with DCM and sat. aq. NaHCO3
  3. concentrationThe organic layer was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b3751a34aa9f43bbba2fcba25ded68ab
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022206B2

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