Pyridine → HCID 25000075, Verbindung

HRID 424144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 424144
C(C1C=C([CH2+]=NC2C=CC(OC3C=CN=C(C(NC)=O)C=3)=CC=2F)N(C2C=[CH:34][CH:33]=[C:32]([CH2:36][OH:37])C=2)N=1)(C)(C)C.[C:38]([C:42]1[CH:46]=[C:45]([NH:47][C:48]([NH:50][C:51]2[CH:67]=[CH:66][C:54]([O:55][C:56]3[CH:61]=[CH:60][N:59]=[C:58]([C:62]([NH:64][CH3:65])=[O:63])[CH:57]=3)=[CH:53][C:52]=2[F:68])=[O:49])[N:44]([C:69]2[CH:74]=[CH:73][CH:72]=[C:71]([CH2:75][OH:76])[CH:70]=2)[N:43]=1)([CH3:41])([CH3:40])[CH3:39].N1C=CC=C[CH:78]=1.CC(C)C(=O)CCl>ClCCl.CCOC(C)=O>[CH3:78][CH:33]([CH3:34])[CH2:32][C:36]([O:76][CH2:75][C:71]1[CH:72]=[CH:73][CH:74]=[C:69]([N:44]2[C:45]([NH:47][C:48](=[O:49])[NH:50][C:51]3[CH:67]=[CH:66][C:54]([O:55][C:56]4[CH:61]=[CH:60][N:59]=[C:58]([C:62](=[O:63])[NH:64][CH3:65])[CH:57]=4)=[CH:53][C:52]=3[F:68])=[CH:46][C:42]([C:38]([CH3:41])([CH3:39])[CH3:40])=[N:43]2)[CH:70]=1)=[O:37]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 124665981-Chloro-3-methylbutan-2-oneHCID 24829325HCID 24829325, Verbindung

Produkt 1

HCID 25000075HCID 25000075, VerbindungAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a 0° C. solution of example 1, (4-{4-[({3-tert-butyl-1-[3-(hydroxymethyl)phenyl]-1H-pyrazol-5-yl}carbamoyl)amino]-3-fluorophenoxy}-N-methylpyridine-2-carboxamide, (0.10 g, 0.19 mmol) in dichloromethane (1.0 mL)/pyridine (0.3 mL) was added dropwise 3-methylbutanonyl chloride (0.02 mL, 0.23 mmol). The reaction mixture was allowed to warm to room temperature and stir for 72 h. The reaction mixture was diluted with EtOAc and washed with sat. aqueous NaHCO3. The combined organic layer was washed with brine, dried and concentrated. The crude material was purified via column chromatography (CH2Cl2: MeOH, 100% CH2Cl2 to 98.5:1.5) to afford 0.02 g (18%) of the desired product as a white solid. MS m/z 617.3 (M+H)+; Retention time (LC-MS): 3.89 min.

Aufarbeitung

  1. washwashed with sat. aqueous NaHCO3
  2. washThe combined organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude material was purified via column chromatography (CH2Cl2: MeOH, 100% CH2Cl2 to 98.5:1.5)

Quellen und Nachweise

ORD-Eintrag
ord-bfe4a251edd14d4c8d50929882aa8c41
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101773B2

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