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Cesium carbonate → (trans)-Naphthalen-2-ylmethyl 3-hydroxy-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate

HRID 1095714
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1095714
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[C:18]([OH:25])[CH:19]=[CH:20][CH:21]=4)[N:16]=3)=[CH:13][N:14]=[C:8]2[CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH:32]12[O:38][CH:37]1[CH2:36][CH2:35][N:34]([C:39]([O:41][CH2:42][C:43]1[CH:52]=[CH:51][C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH:44]=1)=[O:40])[CH2:33]2.[NH4+].[Cl-]>CC(N(C)C)=O.C(Cl)(Cl)Cl>[OH:38][C@H:32]1[C@H:37]([O:25][C:18]2[CH:19]=[CH:20][CH:21]=[C:22]3[C:17]=2[N:16]=[C:15]([C:12]2[N:9]4[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:7][C:8]4=[N:14][CH:13]=2)[CH:24]=[CH:23]3)[CH2:36][CH2:35][N:34]([C:39]([O:41][CH2:42][C:43]2[CH:52]=[CH:51][C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH:44]=2)=[O:40])[CH2:33]1
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Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 66781369HCID 66781369, VerbindungHCID 86638609Naphthalen-2-ylmethyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

Produkt 1

HCID 131729513(trans)-Naphthalen-2-ylmethyl 3-hydroxy-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate
Ausbeute 58,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2-(7-(2-Methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ol (0.10 g, 0.309 mmol) was slurried in DMA (1.0 mL) and treated with Cs2CO3 (0.201 g, 0.618 mmol). After 10 minutes, naphthalen-2-ylmethyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (0.100 g, 0.355 mmol) was added. The reaction was warmed to 90° C. and stirred for 40 hours. The reaction mixture was cooled to ambient temperature then added dropwise into saturated NH4Cl (5 mL). Chloroform (25 mL) was added and the layers were separated. The aqueous layer was washed with CHCl3 and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with a gradient from 1 to 20% (6% NH4OH in MeOH)/ethyl acetate to provide the desired product (111 mg). MS ESI (+) m/z 619.2 (M+1) detected.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customthe layers were separated
  3. washThe aqueous layer was washed with CHCl3
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with a gradient from 1 to 20% (6% NH4OH in MeOH)/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a183488517674e8ebbf3cc0b4c90bae3
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08138181B2

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