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Hydrochloric Acid → 1-methyl-N-(1-methyl-3-(4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazole-3-sulfonamide

HRID 331067
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 331067
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH3:22])[CH:9]=[C:10]([C:11]3[CH:21]=[CH:20][C:14]4[O:15][CH2:16][CH2:17][N:18]([CH3:19])[C:13]=4[CH:12]=3)[C:3]=12.[CH3:23][N:24]1[CH:28]=[CH:27][C:26]([S:29]([NH2:32])(=[O:31])=[O:30])=[N:25]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:23][N:24]1[CH:28]=[CH:27][C:26]([S:29]([NH:32][C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[N:8]([CH3:22])[CH:9]=[C:10]([C:11]4[CH:21]=[CH:20][C:14]5[O:15][CH2:16][CH2:17][N:18]([CH3:19])[C:13]=5[CH:12]=4)[C:3]=23)(=[O:31])=[O:30])=[N:25]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 148356431-methyl-1H-pyrazole-3-sulfonamideHCID 710901456-(4-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine

Produkt 1

HCID 86720296
1-methyl-N-(1-methyl-3-(4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazole-3-sulfonamide
Ausbeute 45,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

6-(4-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine (344 mg, 0.960 mmol), 1-methyl-1H-pyrazole-3-sulfonamide (D94) (186 mg, 1.152 mmol), xantphos (111 mg, 0.192 mmol), palladium(II) acetate (21.56 mg, 0.096 mmol) and cesium carbonate (939 mg, 2.88 mmol) were dissolved in 1,4-dioxane (10 mL) and refluxed at 130° C. overnight. The mixture was cooled and then acidified with 1M HCl till pH7-8. Water (50 mL) was added and extracted with ethyl acetate (3×50 mL). The combined organics were dried over magnesium sulfate, filtered and concentrated. The residue was purified on normal phase silica eluting with a gradient of 0-100% ethyl acetate in cyclohexane to give an impure fraction which was further triturated with MeOH and followed by purification on reverse phase eluting with acetonitrile and water (+0.2% formic acid) to give the title compound (191 mg). LCMS (A): m/z (M+H)+ 439, C21H22N6O3S requires 438 (acidic).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on normal phase silica eluting with a gradient of 0-100% ethyl acetate in cyclohexane
  7. customto give an impure fraction which
  8. customwas further triturated with MeOH
  9. customfollowed by purification on reverse phase
  10. washeluting with acetonitrile and water (+0.2% formic acid)

Quellen und Nachweise

ORD-Eintrag
ord-1ad3fe22cfc143d89e4356f605bb5a70
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08877742B2

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