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Potassium Carbonate → N-[1-{[4-(Aminosulfonyl)phenyl]methyl}-4-(methyloxy)-1H-indazol-3-yl]-5-chloro-2-thiophenesulfonamide

HRID 1808608
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1808608
[Cl:1][C:2]1[S:6][C:5]([S:7]([N:10]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][C:26]=3[O:28][CH3:29])[NH:21][N:20]=2)COCC[Si](C)(C)C)(=[O:9])=[O:8])=[CH:4][CH:3]=1.Br[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([S:38]([NH2:41])(=[O:40])=[O:39])=[CH:34][CH:33]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:41][S:38]([C:35]1[CH:36]=[CH:37][C:32]([CH2:31][N:21]2[C:22]3[C:27](=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][CH:23]=3)[C:19]([NH:10][S:7]([C:5]3[S:6][C:2]([Cl:1])=[CH:3][CH:4]=3)(=[O:9])=[O:8])=[N:20]2)=[CH:33][CH:34]=1)(=[O:39])=[O:40]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium Carbonate2×HCID 131545004-BromomethylbenzenesulfonamideHCID 580544435-chloro-N-[4-(methyloxy)-1H-indazol-3-yl]-N-({[2-(trimethylsilyl)ethyl]oxy}methyl)-2-thiophenesulfonamide2×

Produkt 1

HCID 59456048N-[1-{[4-(Aminosulfonyl)phenyl]methyl}-4-(methyloxy)-1H-indazol-3-yl]-5-chloro-2-thiophenesulfonamideAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Chloro-N-[4-(methyloxy)-1H-indazol-3-yl]-N-({[2-(trimethylsilyl)ethyl]oxy}methyl)-2-thiophenesulfonamide (for a preparation see Intermediate 8) (1.734 g, 3.66 mmol) was dissolved in DMF (2.4 mL) and an aliquot (0.1 mL, 0.15 mmol) added to 4-(bromomethyl)benzenesulfonamide (APAC Pharm) (0.15 mmol) and potassium carbonate (0.15 mmol) added last. The tubes were capped and shaken. Stood at room temperature for 18 h, more potassium carbonate (excess) added and reshaken the tubes. Filtered through alltech tube to remove inorganic solids, and washed tubes with MeOH (1 mL) and blown to dryness under a stream of nitrogen in a Radley's blow down unit. Redissolved in DCM (0.5 mL) and applied to a 10 g silica cartridge, and purified by chromatography on Flashmaster using a gradient of 0-100% DCM-(DCM with 20% EtOAc) over 20 min. The appropriate fractions were combined and evaporated in vacuo using the Genevac. The residue was dissolved in TBAF (1M, 0.5 mL) and heated in a microwave oven (50 Watts, 10 min, at approx 110° C. The sample was purified by MDAP on Atlantis column using Acetonitrile Water with a Formic acid modifier. The solvent was evaporated in vacuo using the Genevac to give the title compound (7.9 mg, 10%) LCMS (System A) RT=0.92 min, ES+ve m/z 513/515 (M+H)+

Aufarbeitung

  1. additionadded last
  2. customThe tubes were capped
  3. filtrationFiltered through alltech tube
  4. customto remove inorganic solids
  5. washwashed tubes with MeOH (1 mL)
  6. dissolutionRedissolved in DCM (0.5 mL)
  7. custompurified by chromatography on Flashmaster
  8. customover 20 min
  9. customevaporated in vacuo
  10. dissolutionThe residue was dissolved in TBAF (1M, 0.5 mL)
  11. temperatureheated in a microwave oven (50 Watts, 10 min
  12. customat approx 110° C
  13. customThe sample was purified by MDAP on Atlantis column
  14. customThe solvent was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-badccc1266414523ac26ee2b283cd736
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08357716B2

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