Tetrahydrofuran → 5-[4-[6-(4-n-Hexylaminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4dione

HRID 412380Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 412380
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12](C(OC(C)(C)C)=O)=[CH:11][C:10]=2NCCCCCC)=[CH:4][C:3]=1[N:29]([CH3:37])[C:30](=O)OC(C)(C)C.[O:38]=[C:39]1[NH:43][C:42](=[O:44])[CH:41]([CH2:45][C:46]2[CH:56]=[CH:55][C:49]([O:50][CH2:51]C(O)=O)=[CH:48][CH:47]=2)[S:40]1.C(P(=O)(OCC)OCC)#N.C([N:69]([CH2:72][CH3:73])CC)C.O1[CH2:78][CH2:77][CH2:76][CH2:75]1>>[CH2:72]([NH:69][C:12]1[CH:11]=[CH:10][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]3[N:1]=[C:37]([CH2:51][O:50][C:49]4[CH:48]=[CH:47][C:46]([CH2:45][CH:41]5[S:40][C:39](=[O:38])[NH:43][C:42]5=[O:44])=[CH:56][CH:55]=4)[N:29]([CH3:30])[C:3]=3[CH:4]=2)=[CH:14][CH:13]=1)[CH2:73][CH2:75][CH2:76][CH2:77][CH3:78]

Komponenten

6

Edukt 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 113234852-(4-((2,4-Dioxothiazolidin-5-YL)methyl)phenoxy)acetic acidHCID 68565430t-butyl N-[2-amino-5-(4-t-butoxycarbonyl-n-hexylaminophenoxy)phenyl]-N-methylcarbamate

Produkt 1

HCID 865877705-[4-[6-(4-n-Hexylaminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4dione

Versuchsvorschrift

A mixture of t-butyl N-[2-amino-5-(4-t-butoxycarbonyl-n-hexylaminophenoxy)phenyl]-N-methylcarbamate (4.10 g), 4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetic acid (2.81 g), diethyl cyanophosphonate (1.63 g), triethylamine (1.01 g) and anhydrous tetrahydrofuran (100 ml) was stirred at room temperature for 28 hours. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The extract was dried over anhydrous sodium sulfate and concentrated. To the residue was added 4N hydrogen chloride in 1,4-dioxane (50 ml) and the mixture was stirred at room temperature for 66 hours. To the reaction mixture was added water and this mixture was neutralized with sodium bicarbonate and extracted with ethyl acetate. The extract was dried over sodium sulfate and concentrated. The residue was chromatographed on a silica gel column using ethyl acetate:n-hexane=3:2 as the eluant to afford the desired compound (2.89 g, mp 177-179° C.).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. additionTo the residue was added 4N hydrogen chloride in 1,4-dioxane (50 ml)
  6. stirringthe mixture was stirred at room temperature for 66 hours
  7. additionTo the reaction mixture was added water
  8. extractionextracted with ethyl acetate
  9. dry with materialThe extract was dried over sodium sulfate
  10. concentrationconcentrated
  11. customThe residue was chromatographed on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-8ab6501c35004233bdee422afa7561bf
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562849B1

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