Sodium Chloride → HCID 178509115, Verbindung

HRID 2261686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2261686
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([CH:7]2[CH2:12][CH2:11][N:10](C(=O)C)[CH2:9][CH2:8]2)[C:3]=1[C:16]1[S:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1.[OH-].[Na+].[Na+].[Cl-]>Cl>[NH3:1].[S:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[C:3]1[C:4]([CH:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)=[N:5][NH:6][C:2]=1[NH2:1]

Komponenten

6

Edukt 3

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 178473791HCID 178473791, Verbindung

Produkt 2

HCID 222AmmoniaAusbeute 1 %HCID 178509115HCID 178509115, VerbindungAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

A solution of the above prepared 1-[4-(5-amino-4-benzothiazol-2-yl-1H-pyrazol-3-yl)-piperidin-1-yl]-ethanone (54 mg, 0.158 mmol) in 6N HCl (10 mL) was refluxed for 6 hrs and was allowed to cool to room temperature overnight. The resulting mixture was poured over crushed ice (20 mL) and the solution was adjusted to neutral pH using a 10% NaOH solution. The resulting solution was saturated with NaCl and was extracted with ethyl acetate (10×50 mL). The combined extracts were washed once with brine, dried over anhydrous sodium sulfate, filtered and evaporated. The resulting crude product was purified by flash column chromatography eluting with CH2Cl2:MeOH=20:1 with 1% ammonia to yield 15 mg (32%) of the title compound. MS (m/z, ES+): 300.14 (M+1, 100%).

Aufarbeitung

  1. temperaturewas refluxed for 6 hrs
  2. additionThe resulting mixture was poured
  3. extractionwas extracted with ethyl acetate (10×50 mL)
  4. washThe combined extracts were washed once with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting crude product was purified by flash column chromatography
  9. washeluting with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-e5d802c442264070821c6698c1450e99
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07847101B2

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