Aluminium lithium hydride → N-{[3-({4-(Methyloxy)-3-[(2-thienylsulfonyl)amino]-1H-indazol-1-yl}methyl)phenyl]methyl}acetamide

HRID 1892964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1892964
Cl[C:2]1[S:6][C:5]([S:7]([NH:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[O:20][CH3:21])[N:13]([CH2:22][C:23]3[CH:24]=[C:25]([CH2:29][NH:30][C:31](=[O:33])[CH3:32])[CH:26]=[CH:27][CH:28]=3)[N:12]=2)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:21][O:20][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:19]=1[C:11]([NH:10][S:7]([C:5]1[S:6][CH:2]=[CH:3][CH:4]=1)(=[O:8])=[O:9])=[N:12][N:13]2[CH2:22][C:23]1[CH:24]=[C:25]([CH2:29][NH:30][C:31](=[O:33])[CH3:32])[CH:26]=[CH:27][CH:28]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 59456102N-[(3-{[3-{[(5-Chloro-2-thienyl)sulfonyl]amino}-4-(methyloxy)-1H-indazol-1-yl]methyl}phenyl)methyl]acetamide

Produkt 1

HCID 59456004N-{[3-({4-(Methyloxy)-3-[(2-thienylsulfonyl)amino]-1H-indazol-1-yl}methyl)phenyl]methyl}acetamideAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cooled (ice/water bath) solution of N-[(3-{[3-{[(5-chloro-2-thienyl)sulfonyl]amino}-4-(methyloxy)-1H-indazol-1-yl]methyl}phenyl)methyl]acetamide (for a preparation see Example 1) (30 mg, 0.06 mmol) in THF (1 mL) was added dropwise 2M lithium aluminium hydride in THF (0.074 mL, 0.149 mmol), and the suspension was stirred 10 min at 0° C. and then at room temperature for one hour. Reaction was quenched with 4 drops of water and then with aqueous solution of sodium hydroxide (2M, 0.5 mL). After stirring for 30 min, solid was removed and washed with THF (10 mL). The filtrate was concentrated under reduced pressure and the residue was dissolved in 1:1 MeOH-DMSO (1 mL) and purified by Mass Directed AutoPrep on Sunfire C18 column using Acetonitrile Water with a TFA modifier (Method B). The solvent from appropriate fractions was evaporated under a stream of nitrogen in a Radleys blowdown apparatus to give the title compound (18 mg, 64%). LCMS (System A) RT=0.89 min, ES+ve m/z 471 (M+H)+.

Aufarbeitung

  1. waitat room temperature for one hour
  2. customReaction
  3. customwas quenched with 4 drops of water
  4. stirringAfter stirring for 30 min
  5. customsolid was removed
  6. washwashed with THF (10 mL)
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. dissolutionthe residue was dissolved in 1:1 MeOH-DMSO (1 mL)
  9. custompurified by Mass Directed AutoPrep on Sunfire C18 column
  10. customThe solvent from appropriate fractions was evaporated under a stream of nitrogen in a Radleys blowdown apparatus

Quellen und Nachweise

ORD-Eintrag
ord-2958c3bfa9de4a978402cbca775793c1
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507543B2

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