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Hydrochloric Acid → HCID 178483082, Verbindung

HRID 1984875
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1984875
C(OC(=O)[NH:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15][C:16]2[N:25]=[C:24]([N:26]([CH3:28])[CH3:27])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)[CH2:11][CH2:10]1)(C)(C)C.Cl.C(N(C(C)C)CC)(C)C.[Br:40][C:41]1[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[C:43]([O:51][C:52]([F:55])([F:54])[F:53])[CH:42]=1>CCOC(C)=O.C(Cl)Cl>[Br:40][C:41]1[CH:46]=[CH:45][C:44]([S:47]([NH:7][CH2:8][C@H:9]2[CH2:10][CH2:11][C@H:12]([NH:15][C:16]3[N:25]=[C:24]([N:26]([CH3:28])[CH3:27])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=3)[CH2:13][CH2:14]2)(=[O:49])=[O:48])=[C:43]([O:51][C:52]([F:55])([F:54])[F:53])[CH:42]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 81531Diisopropylethylamine2×HCID 27364214-Bromo-2-(Trifluoromethoxy)Benzene-1-Sulfonyl Chloride2×HCID 178483080HCID 178483080, Verbindung

Produkt 1

HCID 178483082HCID 178483082, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 6344DichloromethaneLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a suspension of trans-[4-(4-dimethylamino-quinazolin-2-ylamino)-cyclohexylmethyl]-carbamic acid tert-butyl ester (500 mg, 1.25 mmol) in EtOAc (5 mL) was added 4 M hydrogen chloride in EtOAc (5 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated to give a white solid. To a suspension of the above solid in CH2Cl2 (7 mL) was added diisopropylethylamine (905 μL, 5.20 mmol). The mixture was cooled to 4° C. and a solution of 4-bromo-2-trifluoromethoxy-benzenesulfonyl chloride (446 mg, 1.31 mmol) in CH2Cl2 (2 mL) was added below 5° C. The reaction mixture was stirred at 4° C. for 1.5 hr. To the reaction mixture was added a solution of 4-bromo-2-trifluoromethoxy-benzenesulfonyl chloride (85 mg, 0.25 mmol) in CH2Cl2 (0.5 mL) and the mixture was stirred at 4° C. for 1 hr. To the reaction mixture was added diisopropylethylamine (220 μL, 1.26 mmol) and the mixture was stirred at 4° C. for 1 hr. The reaction was quenched with saturated aqueous NaHCO3. The aqueous layer was extracted with CHCl3 (three times). The combined organic layer was dried over MgSO4, filtered, concentrated, and purified by flash chromatography (NH-silica gel, 50% EtOAc in hexane) to give trans-4-bromo-N-[4-(4-dimethylamino-quinazolin-2-ylamino)-cyclohexylmethyl]-2-trifluoromethoxy-benzenesulfonamide (624 mg, 83%) as a pale yellow solid.

Aufarbeitung

  1. concentrationconcentrated
  2. customto give a white solid
  3. temperatureThe mixture was cooled to 4° C.
  4. stirringThe reaction mixture was stirred at 4° C. for 1.5 hr
  5. stirringthe mixture was stirred at 4° C. for 1 hr
  6. stirringthe mixture was stirred at 4° C. for 1 hr
  7. customThe reaction was quenched with saturated aqueous NaHCO3
  8. extractionThe aqueous layer was extracted with CHCl3 (three times)
  9. dry with materialThe combined organic layer was dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. custompurified by flash chromatography (NH-silica gel, 50% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-72b5fcdd57c14018b555336494b668f7
Quelldatensatz
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07544690B2

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