Water → 4-oxo-N-(6-(pyrrolidin-1-ylmethyl)pyridin-2-yl)-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carboxamide

HRID 876540Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 876540
CCN(C(C)C)C(C)C.[O:10]=[C:11]1[C:20]2[C:15](=[C:16]([C:21](Cl)=[O:22])[CH:17]=[CH:18][CH:19]=2)[O:14][C:13]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)=[CH:12]1.Cl.[N:35]1([CH2:40][C:41]2[N:46]=[C:45]([NH2:47])[CH:44]=[CH:43][CH:42]=2)[CH2:39][CH2:38][CH2:37][CH2:36]1.O>CC#N>[O:10]=[C:11]1[C:20]2[C:15](=[C:16]([C:21]([NH:47][C:45]3[CH:44]=[CH:43][CH:42]=[C:41]([CH2:40][N:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)[N:46]=3)=[O:22])[CH:17]=[CH:18][CH:19]=2)[O:14][C:13]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)=[CH:12]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 584773264-oxo-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carbonyl chlorideHCID 672957736-(Pyrrolidin-1-ylmethyl)pyridin-2-amine hydrochloride

Produkt 1

HCID 584772604-oxo-N-(6-(pyrrolidin-1-ylmethyl)pyridin-2-yl)-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carboxamideAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

DIPEA (125 mL, 0.705 mmol) was added to a solution of 4-oxo-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carbonyl chloride 37 (83 mg, 0.235 mmol) and 6-(pyrrolidin-1-ylmethyl)pyridin-2-amine hydrochloride 49 (75 mg, 0.353 mmol) in CH3CN (15 mL). The reaction mixture was heated at 60° C. for 12 h, cooled to room temperature and poured into H2O. The mixture was extracted with CH2Cl2. The combined organics were dried (MgSO4) and concentrated. The crude residue was purified by MPLC eluting with CH2Cl2/MeOH (0-10%) to give Compound 243 (46 mg, 40% yield). MS (ESI) calcd for C27H22F3N3O3: 493.16. found: 494 [M+H].

Aufarbeitung

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with CH2Cl2
  3. dry with materialThe combined organics were dried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified by MPLC
  6. washeluting with CH2Cl2/MeOH (0-10%)

Quellen und Nachweise

ORD-Eintrag
ord-14e86065c53b41069cb0314a66020b16
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987258B2

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