Hydrochloric Acid → 2-[(1R)-5-(5-Ethylpyrimidin-2-yl)-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane dihydrochloride

HRID 1913453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1913453
[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C@H:14]([N:18]2[CH2:21][C:20]4([CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]4)[CH2:19]2)[CH2:13][CH2:12]3)=[N:7][CH:8]=1)[CH3:2].[ClH:34].CO>O1CCOCC1>[ClH:34].[ClH:34].[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C@H:14]([N:18]2[CH2:21][C:20]4([CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)[CH2:19]2)[CH2:13][CH2:12]3)=[N:7][CH:8]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 58438491tert-butyl 2-[(1R)-5-(5-ethylpyrimidin-2-yl)-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane-7-carboxylate

Produkt 1

HCID 674091552-[(1R)-5-(5-Ethylpyrimidin-2-yl)-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane dihydrochlorideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a flask charged with tert-butyl 2-[(1R)-5-(5-ethylpyrimidin-2-yl)-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane-7-carboxylate (3-1b, 583 mg, 1.39 mmol) was added 8.0 mL of 4N HCl in dioxane at room temperature. A yellow precipitate formed immediately after the addition. The mixture was stirred at room temperature for 40 minutes. Anhydrous methanol (4 mL) was added to solublize the reaction. The resulting solution was stirred at room temperature for 4 hours. Solvent and excess HCl were removed and dried in vacuo to afford 630 mg (100%) of a light yellow solid (3-1c). The crude product was taken on to the next step without further purification. MS (ES+) 349.4 (M+H)+. 1H NMR (CD3OD) δ 1.40 (t, 3H) 2.21-2.28 (m, 5H) 2.61 (br s, 1H) 2.93 (q, 2H) 3.16-3.34 (m, 4H), 3.38-3.51 (m, 1H), 4.12-4.29 (m, 4H) 4.52-4.56 (m, 1H) 5.08-5.12 (m, 1H) 7.89-7.93 (m, 1H) 8.29-8.33 (m, 2H), 9.15-9.19 (m, 2H).

Aufarbeitung

  1. customA yellow precipitate formed immediately
  2. additionafter the addition
  3. customthe reaction
  4. stirringThe resulting solution was stirred at room temperature for 4 hours
  5. customSolvent and excess HCl were removed
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c14987e7e44341189ee711d8f69cdabe
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609680B2

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