Hydrochloric Acid → HCID 67429444, Verbindung

HRID 410703Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 410703
[CH3:1][C:2]1([CH3:36])[C:11]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[C:22]([NH:24][C:25]4[N:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][N:26]=4)[CH:21]=[C:20]([CH3:35])[CH:19]=3)=[CH:16][N:17]=2)([OH:12])[CH2:10][CH2:9][CH2:8][C:3]21OCC[O:4]2.Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[OH:12][C:11]1([C:13]2[S:14][C:15]([C:18]3[CH:23]=[C:22]([NH:24][C:25]4[N:30]=[C:29]([C:31]([F:33])([F:34])[F:32])[CH:28]=[CH:27][N:26]=4)[CH:21]=[C:20]([CH3:35])[CH:19]=3)=[CH:16][N:17]=2)[CH2:10][CH2:9][CH2:8][C:3](=[O:4])[C:2]1([CH3:36])[CH3:1]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 67432981HCID 67432981, Verbindung

Produkt 1

HCID 67429444HCID 67429444, VerbindungAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of the product of Step 1(600 mg, 1.15 mmol) in THF (4 mL) was added HCl (6 M, 3.84 mL, 23.1 mmol). The reaction mixture was allowed to stir at room temperature for 30 min, neutralized with aqueous saturated sodium bicarbonate, and extracted with dichloromethane (3×). The combined organics were dried (sodium sulfate), filtered, concentrated, and purified by flash chromatography on silica to afford 3-hydroxy-2,2-dimethyl-3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclohexanone (534 mg, 1.12 mmol) as a yellow foam. MS ESI: [M+H]+ m/z 477.1.

Aufarbeitung

  1. extractionextracted with dichloromethane (3×)
  2. dry with materialThe combined organics were dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-5cfdf26549a4451293aa141fedeee2c2
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759366B2

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