1-Methylpiperazine → 4-(3-Chloro-phenyl)-2-[5-methoxy-6-(4-methyl-piperazin-1-ylmethyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid amide

HRID 1667788Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667788
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([N:16]3[C:20]4[CH:21]=[C:22]([CH:27]=O)[C:23]([O:25][CH3:26])=[CH:24][C:19]=4[N:18]=[CH:17]3)[S:11][C:12]=2[C:13]([NH2:15])=[O:14])[CH:5]=[CH:6][CH:7]=1.[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([N:16]3[C:20]4[CH:21]=[C:22]([CH2:27][N:33]5[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]5)[C:23]([O:25][CH3:26])=[CH:24][C:19]=4[N:18]=[CH:17]3)[S:11][C:12]=2[C:13]([NH2:15])=[O:14])[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 866428484-(3-Chloro-phenyl)-2-(6-formyl-5-methoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide

Produkt 1

HCID 468320404-(3-Chloro-phenyl)-2-[5-methoxy-6-(4-methyl-piperazin-1-ylmethyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 0.053 g (0.13 mmole) of 4-(3-chloro-phenyl)-2-(6-formyl-5-methoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide (I.46a), 0.030 mL of N-methylpiperazine, 0.050 g of sodium triacetoxyborohydride and 5 mL of dichloromethane was stirred at room temperature for 16 hours. The mixture was partitioned between 50 mL of dilute aqueous potassium carbonate solution and 50 mL of dichlormethane. The organic layer was separated and the aqueous layer was extracted three times with 20 mL of dichloromethane. The combined organic layers were washed with 30 mL of brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with methanol-dichloromethane (gradient 15:85-20:80) to give 0.016 g of 4-(3-chloro-phenyl)-2-[5-methoxy-6-(4-methyl-piperazin-1-ylmethyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid amide (I.46) as a pink solid. MH+/Z=497

Aufarbeitung

  1. customThe mixture was partitioned between 50 mL of dilute aqueous potassium carbonate solution and 50 mL of dichlormethane
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted three times with 20 mL of dichloromethane
  4. washThe combined organic layers were washed with 30 mL of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with methanol-dichloromethane (gradient 15:85-20:80)

Quellen und Nachweise

ORD-Eintrag
ord-b34d8c75269e4af884f12913d7d35c9d
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044213B2

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