Phenyl chloroformate → HCID 59379937, Verbindung

HRID 2353729Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2353729
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[F:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([C:21]([C:24]2[CH:29]=[C:28]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][C@@H:31]3[CH3:36])[N:27]=[C:26]([C:37]3[CH:43]=[CH:42][C:40]([NH2:41])=[CH:39][CH:38]=3)[N:25]=2)([CH3:23])[CH3:22])(=[O:20])=[O:19])=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1>[F:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([C:21]([C:24]2[CH:29]=[C:28]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][C@@H:31]3[CH3:36])[N:27]=[C:26]([C:37]3[CH:38]=[CH:39][C:40]([NH:41][C:2](=[O:3])[O:4][C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:42][CH:43]=3)[N:25]=2)([CH3:22])[CH3:23])(=[O:19])=[O:20])=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59379869HCID 59379869, Verbindung

Produkt 1

HCID 59379937HCID 59379937, VerbindungAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Phenyl chloroformate (0.482 mL, 3.83 mmol) was added dropwise to 4-[4-[2-(4-fluorophenyl)sulfonylpropan-2-yl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]aniline (1.8 g, 3.83 mmol) and sodium bicarbonate (0.482 g, 5.74 mmol) in dioxane (20 mL) under nitrogen. The resulting suspension was stirred at RT for 2 hours. The reaction mixture was evaporated to dryness and redissolved in DCM (50 mL) and washed with water (50 mL). The organic layer was dried (MgSO4), filtered and evaporated to give crude product which was triturated with diethyl ether to give the desired material as a white solid (2.26 g).

Aufarbeitung

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionredissolved in DCM (50 mL)
  3. washwashed with water (50 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give crude product which
  8. customwas triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-2ece19b68d18457ba377f6c07b8d0764
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07750003B2

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