Ethyl Acetate → N-(3-(3-(1-(3-nitrobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methane sulfonamide

HRID 531481Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 531481
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:13]=[C:14]3[C:20]([C:21]4[CH:22]=[N:23][N:24]([CH2:26][C:27]5[CH:32]=[CH:31][CH:30]=[C:29]([N+:33]([O-:35])=[O:34])[CH:28]=5)[CH:25]=4)=[CH:19][N:18](C(OC(C)(C)C)=O)[C:15]3=[N:16][CH:17]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:4])=[O:3].O1CCOCC1.Cl.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>CO.CCCCCC>[N+:33]([C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][CH:30]=1)[CH2:26][N:24]1[CH:25]=[C:21]([C:20]2[C:14]3[C:15](=[N:16][CH:17]=[C:12]([C:8]4[CH:7]=[C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:11]=[CH:10][CH:9]=4)[CH:13]=3)[NH:18][CH:19]=2)[CH:22]=[N:23]1)([O-:35])=[O:34]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 118523971tert-butyl 5-(3-(methylsulfonamido)phenyl)-3-(1-(3-nitrobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Produkt 1

HCID 72944751N-(3-(3-(1-(3-nitrobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methane sulfonamideAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

tert-butyl 5-(3-(methylsulfonamido)phenyl)-3-(1-(3-nitrobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (200 mg, 0.409 mmol) dissolved in 10 ml of methanol and added 1,4-dioxane/HCl (2 ml) at 0° C. and stirred at room temperature for 15 h. The reaction was monitored by TLC (30% ethyl acetate in hexane). The reaction mixture was concentrated under reduced pressure to afford crude product. The residue was basified with saturated sodium bicarbonate solution and extracted with ethyl acetate (2×25 ml). The organic layer was dried over Na2SO4, and concentrated under reduced pressure to afford 100 mg (62% yield) of the pure required product. 1H NMR (DMSO-d6, 400 MHz): δ11.82 (s, 1H), 9.85 (s, 1H), 8.47 (s, 2H), 8.33 (s, 1H), 8.18-8.15 (d, 2H), 8.00 (s, 1H), 7.806-7.7.800 (d, 1H), 7.75-7.34 (d, 1H), 7.69-7.65 (t, 1H), 7.52-7.44 (m, 3H), 7.24-7.22 (d, 1H), 5.55 (s, 2H), 3.05 (s, 3H). MS: m/z=489.3 (M+1), HPLC: 93.67% (method B).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto afford crude product
  3. extractionextracted with ethyl acetate (2×25 ml)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ff74954c89784a45a2a2b77d0aa63a71
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353107B2

Notizen zur Reaktion

Wird geladen…