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Water → 1-(benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-6-fluoro-1-(2-hydroxyethyl)-1H-indol-5-yl)cyclopropanecarboxamide

HRID 1847551
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Reaktionsgleichung

Reaktionsgleichung von HRID 1847551
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][C:24]=4[F:25])[NH:21][CH:20]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:19]5)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[CH:30]([CH:32]=O)=[O:31].O.[BH3-]C#N.[Na+]>CO.CC#N.O.C(O)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][C:24]=4[F:25])[N:21]([CH2:32][CH2:30][OH:31])[C:20]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:19]5)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1
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Komponenten

8

Edukt 4

HCID 962WaterHCID 7860GlyoxalHCID 5003444Sodium cyanoborohydrideHCID 59129318HCID 59129318, Verbindung

Produkt 1

HCID 591291721-(benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-6-fluoro-1-(2-hydroxyethyl)-1H-indol-5-yl)cyclopropanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176
Acetic Acid
Lösungsmittel
HCID 887MethanolLösungsmittel
HCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of 1-(benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-6-fluoroindolin-5-yl)cyclopropanecarboxamide (340 mg, 0.86 mmol) in anhydrous MeOH (5.7 mL) containing 1% of acetic acid was added glyoxal 40% in water (0.60 mL, 5.2 mmol) at room temperature under N2. After 20 min of stirring, NaBH3CN (120 mg, 1.9 mmol) was added in one portion and the reaction mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure and the residue obtained was purified by column chromatography on silica gel (10-40% ethyl acetate/hexanes) providing a pale yellow oil which was treated with 50/50 CH3CN—H2O containing 0.05% TFA and CDCl3. Solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (20-35% ethyl acetate/hexanes) to give 1-(benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-6-fluoro-1-(2-hydroxyethyl)-1H-indol-5-yl)cyclopropanecarboxamide. 1H NMR (400 MHz, CDCl3) δ 8.02 (d, J=7.7 Hz, 1H), 7.30 (d, J=2.1 Hz, 1H), 6.93 (dd, J=1.6, 7.9 Hz, 1H), 6.90 (d, J=1.6 Hz, 1H), 6.90 (d, J=1.6 Hz, 1H), 6.78 (d, J=7.9 Hz, 1H), 6.08 (s, 1H), 5.92 (s, 2H), 4.21 (dd, J=6.9, 6.9 Hz, 2H), 3.68 (m, 2H), 2.28 (s, 1H), 1.60 (dd, J=3.7, 6.7 Hz, 2H), 1.35-1.32 (m, 9H), 1.04 (dd, J=3.7, 6.8 Hz, 2H). MS (ESI) m/e (M+H+) 439.0.

Aufarbeitung

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. customThe solvent was removed under reduced pressure
  3. customthe residue obtained
  4. customwas purified by column chromatography on silica gel (10-40% ethyl acetate/hexanes)
  5. customproviding a pale yellow oil which
  6. customSolvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (20-35% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a4039b50277e4ce59acb4324135a59ec
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08952050B2

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