Diisopropylethylamine → 5-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid ((1S,2S)-2-hydroxy-cyclohexyl)-amide

HRID 2245264Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2245264
N1C2C(=NC=CC=2)N([N:10]2[C:14](/[CH:15]=[C:16]3\[C:17](=[O:26])[NH:18][C:19]4[C:24]\3=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)=[C:13]([CH3:27])[C:12]([C:28]([O-])=[O:29])=[C:11]2[CH3:31])N=1.CCN(C(C)C)C(C)C.[NH2:41][C@H:42]1[CH2:47][CH2:46][CH2:45][CH2:44][C@@H:43]1[OH:48]>CN(C=O)C>[OH:48][C@H:43]1[CH2:44][CH2:45][CH2:46][CH2:47][C@@H:42]1[NH:41][C:28]([C:12]1[C:13]([CH3:27])=[C:14](/[CH:15]=[C:16]2\[C:17](=[O:26])[NH:18][C:19]3[C:24]\2=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[NH:10][C:11]=1[CH3:31])=[O:29]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 7057408(1S,2S)-2-aminocyclohexanolHCID 131727992(Z)-3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylate

Produkt 1

HCID 592159155-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid ((1S,2S)-2-hydroxy-cyclohexyl)-amideAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To the solution of A4 (100 mg, 0.24 mmol) and DIEA (140 mg, 0.96 mmol) in 10 mL of DMF, was added (1S,2S)-2-Amino-cyclohexanol (45 mg, 0.29 mmol). The reaction mixture was stirred at room temperature for several hours. LC/MS was applied to determine completion of the reaction. DMF was evaporated under reduced pressure and the residue was precipitated with 5% diethylamine/methanol (25 mL) under sonication. The solid was collected by filtration and washed with methanol), dried under vacuum to provide to provide title compound (70 mg, 74% yield) as orange solid. 1H NMR (300 MHz, DMSO-d6): δ=13.62 (s, 1H), 10.88 (s, 1H), 7.71-7.77 (m, 2H), 7.36-7.39 (d, 1H), 6.81-6.95 (m, 2H), 4.58-4.60 (d, 1H), 3.48-3.60 (m, 1H), 3.30-3.35 (m, 1H), 2.41-2.44 (ds, 6H), 1.88-1.90 (t, 2H), 1.62 (S, 2 h), 1.23 (s, 4H). LC/MS: 398.1 [M+H]+.

Aufarbeitung

  1. customcompletion of the reaction
  2. customDMF was evaporated under reduced pressure
  3. customthe residue was precipitated with 5% diethylamine/methanol (25 mL) under sonication
  4. filtrationThe solid was collected by filtration
  5. washwashed with methanol),
  6. customdried under vacuum
  7. customto provide

Quellen und Nachweise

ORD-Eintrag
ord-ed75fda612354cefa0a1595f8e42124a
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07683057B2

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