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Potassium Hydroxide → 4-{[3-Amino-4-(methyloxy)-1H-indazol-1-yl]methyl}benzamide

HRID 1874677
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1874677
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([NH2:12])=[N:6][NH:7]2.CC(N(CC1C=CC(CN2C3C(=C(OC)C=CC=3)C(NS(C3SC(Cl)=CC=3)(=O)=O)=N2)=CC=1)C(=O)[O-])(C)C.[OH-].[K+].Cl[CH2:53][C:54]1[CH:62]=[CH:61][C:57]([C:58]([NH2:60])=[O:59])=[CH:56][CH:55]=1>CS(C)=O.O>[NH2:12][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[CH:11][C:3]=2[O:2][CH3:1])[N:7]([CH2:53][C:54]2[CH:62]=[CH:61][C:57]([C:58]([NH2:60])=[O:59])=[CH:56][CH:55]=2)[N:6]=1
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Komponenten

7

Edukt 4

HCID 14797Potassium HydroxideHCID 4583634-(Chloromethyl)benzamideHCID 185260534-Methoxy-1H-indazol-3-amineHCID 866614021,1-dimethylethyl[(4-{[3-{[(5-chloro-2-thienyl)sulfonyl]amino}-4-(methyloxy)-1H-indazol-1-yl]methyl}phenyl)methyl]carbamate

Produkt 1

HCID 580545244-{[3-Amino-4-(methyloxy)-1H-indazol-1-yl]methyl}benzamide
Ausbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 4-(methyloxy)-1H-indazol-3-amine (for a preparation see Intermediate 1) (0.816 g, 5 mmol) in DMSO (50 mL) at room temperature under nitrogen was added potassium hydroxide (0.561 g, 10.0 mmol). After stirring the resulting deep red solution for 25 min 4-(chloromethyl)benzamide (0.848 g, 5.00 mmol) was added in one portion. The reaction mixture was stirred for a further 30 min and then poured into water (250 mL), forming an emulsion. The reaction mixture was extracted using chloroform (3×250 mL). The combined organic solutions were washed with water (250 mL) and passed through hydrophobic frit. The solvent was removed in vacuo and the residue was loaded in dichloromethane to a silica (100 g) cartridge and purified by chromatography on Flashmaster eluting with 0-100% ethyl acetate-cyclohexane+0-20% methanol-ethyl acetate over 60 min. The appropriate fractions were combined and evaporated in vacuo to give the title compound (1.18 g, 80%). LCMS: (System A) RT=0.69 min, ES+ve m/z 297 (M+H)+.

Aufarbeitung

  1. customat room temperature
  2. additionwas added in one portion
  3. customforming an emulsion
  4. extractionThe reaction mixture was extracted
  5. washThe combined organic solutions were washed with water (250 mL)
  6. customThe solvent was removed in vacuo
  7. custompurified by chromatography on Flashmaster
  8. washeluting with 0-100% ethyl acetate-cyclohexane+0-20% methanol-ethyl acetate over 60 min
  9. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e8e6e03f4430498e8989f5a85d2bad7b
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08304446B2

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