Sodium Thiosulfate → {2-Amino-5-[1-tert-butyl-2-(2-1,2,4-triazol-1-yl-phenyl)-1H-benzimidazol-5-yl]-pyridin-3-yl}-methanol

HRID 1966692Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1966692
[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[C:12]([NH2:21])[CH:11]=2)=[CH:4][N:3]=1.[N:22]1([C:27]2[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=2[CH:29]=O)[CH:26]=[N:25][CH:24]=[N:23]1.OOS([O-])=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C.O>[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]3[N:16]([C:17]([CH3:18])([CH3:20])[CH3:19])[C:29]([C:28]4[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=4[N:22]4[CH:26]=[N:25][CH:24]=[N:23]4)=[N:21][C:12]=3[CH:11]=2)=[CH:4][N:3]=1

Komponenten

7

Edukt 4

HCID 24477Sodium ThiosulfateHCID 35364462-(1H-1,2,4-Triazol-1-yl)benzaldehydeHCID 23707502Potassium hydroxy sulfiteHCID 58542055[2-Amino-5-(3-amino-4-tert-butylamino-phenyl)-pyridin-3-yl]-methanol

Produkt 1

HCID 58541945{2-Amino-5-[1-tert-butyl-2-(2-1,2,4-triazol-1-yl-phenyl)-1H-benzimidazol-5-yl]-pyridin-3-yl}-methanolAusbeute 10,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of [2-amino-5-(3-amino-4-tert-butylamino-phenyl)-pyridin-3-yl]-methanol (100 mg, 0.35 mmol) in DMF (5 mL) is added 2-[1,2,4]-triazol-1-yl-benzaldehyde (73 mg, 0.42 mmol) at room temperature. Oxone (215 mg, 0.35 mmol) in H2O (1 mL) is added and the solution is stirred for 4 hours. Saturated sodium thiosulfate solution (5 mL) is added and the mixture is extracted with EtOAc (3×10 mL) and H2O (10 mL). The combined organic layer is dried with MgSO4 and is filtered. The filtrate is concentrated and the residue is purified by silica gel flash column chromatography eluting with 10% MeOH in CH2Cl2 to afford the title compound (16 mg, 10%) as a pale brown foam. LCMS (ESMS): m/z 440.20 (M++1)

Aufarbeitung

  1. extractionthe mixture is extracted with EtOAc (3×10 mL) and H2O (10 mL)
  2. dry with materialThe combined organic layer is dried with MgSO4
  3. filtrationis filtered
  4. concentrationThe filtrate is concentrated
  5. customthe residue is purified by silica gel flash column chromatography
  6. washeluting with 10% MeOH in CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-bdb04b5e2e3e4fec826fa91a277a3aa3
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420655B2

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