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Ethanol → 6-((1R,2S)-2-Aminocyclohexylamino)-7-fluoro-4-(isothiazol-5-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one

HRID 2173068
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2173068
C(OC([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[N:21]=[C:20]([C:22]2[S:26][N:25]=[CH:24][CH:23]=2)[C:19]2[C:27](=[O:37])[N:28](C(OC(C)(C)C)=O)[CH2:29][C:18]=2[C:17]=1[F:38])=O)(C)(C)C.Cl.O1CCOCC1.CCO>CO>[NH2:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[N:21]=[C:20]([C:22]2[S:26][N:25]=[CH:24][CH:23]=2)[C:19]2[C:27](=[O:37])[NH:28][CH2:29][C:18]=2[C:17]=1[F:38]
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Komponenten

5

Edukt 3

HCID 702EthanolHCID 204431481,4-Dioxane hydrochlorideHCID 71164908tert-butyl 6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-7-fluoro-4-(isothiazol-5-yl)-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate

Produkt 1

HCID 711649406-((1R,2S)-2-Aminocyclohexylamino)-7-fluoro-4-(isothiazol-5-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-oneAusbeute 44,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred solution of tert-butyl 6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-7-fluoro-4-(isothiazol-5-yl)-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (65.9 mg, 0.120 mmol) in MeOH (1.0 mL) was added 4N HCl/dioxane (1.0 mL, 4.00 mmol). The reaction mixture was heated to 60° C. for 1 hour and was subsequently concentrated in vacuo. The residue was triturated with EtOAc and filtered. The filter cake was washed with EtOAc to give a yellow solid, which was suspended into EtOH. The mixture was stirred at 80° C. for 30 minutes and allowed to cool to room temperature. The resulting precipitate was collected by filtration and washed with EtOH to yield a hydrochloride salt of the title compound as an off-white solid (18.6 mg, 40%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.36-1.55 (m, 2H), 1.58-2.06 (m, 6H), 3.77 (br s, 1H), 4.17-4.33 (m, 1H), 4.39-4.54 (m, 2H), 7.19 (d, J=5.86 Hz, 1H), 7.88 (br s, 3H), 8.62 (d, J=1.95 Hz, 1H), 8.69 (s, 1H), 8.97 (d, J=1.95 Hz, 1H). ESI-MS m/z [M+H]+ calc'd for C16H18FN5OS, 348. found, 348.

Aufarbeitung

  1. concentrationwas subsequently concentrated in vacuo
  2. customThe residue was triturated with EtOAc
  3. filtrationfiltered
  4. washThe filter cake was washed with EtOAc
  5. customto give a yellow solid, which
  6. temperatureto cool to room temperature
  7. filtrationThe resulting precipitate was collected by filtration
  8. washwashed with EtOH

Quellen und Nachweise

ORD-Eintrag
ord-bb3999ec80694793a2f0dd62fcd3ae05
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09056873B2

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