1-Hydroxybenzotriazole → 4-(5-Chlorobenzimidazol-2-yl)-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-benzamide

HRID 1352663

Reaktionsgleichung

Reaktionsgleichung von HRID 1352663
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([C:9]3[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=3)[NH:8][C:4]=2[CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH3:42][N:43]1[C:48]([CH3:50])([CH3:49])[CH2:47][CH:46]([NH2:51])[CH2:45][C:44]1([CH3:53])[CH3:52]>C1COCC1.CC#N>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[CH:11][C:12]([C:13]([NH:51][CH:46]4[CH2:45][C:44]([CH3:52])([CH3:53])[N:43]([CH3:42])[C:48]([CH3:50])([CH3:49])[CH2:47]4)=[O:15])=[CH:16][CH:17]=3)[NH:8][C:4]=2[CH:3]=1

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 3763514-(5-chloro-1H-benzimidazol-2-yl)benzoic acidHCID 6937924-Amino-1,2,2,6,6-pentamethylpiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 98452844-(5-Chlorobenzimidazol-2-yl)-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-benzamideAusbeute 50,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of 4-(5-chlorobenzimidazol-2-yl)benzoic acid (0.5 g, 1.63 mmol), 1-hydroxybenzotriazole (0.242 g, 1.79 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.34 g, 1.89 mmol) in THF (15 ml) was heated for 1 h at 35–40° C. 1,2,2,6,6-Pentamethyl-4-aminopiperidine (0.333 g, 1.96 mmol) in THF (3 ml) was added dropwise and the reaction was left 1 h at 60° C. After cooling, the solvent was removed under reduced pressure and the residue was treated with 2N NaOH (15 ml) and extracted with ethyl acetate (20 ml). the organic layer was washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure to give a residue that was treated with CH3CN. The suspension was stirred for 1 h, filtered and dried at 50° C. to give 0.35 g of the title compound (yield 50.5%) as a yellow solid, mp>250° C.

Aufarbeitung

  1. temperaturewas heated for 1 h at 35–40° C
  2. temperatureAfter cooling
  3. customthe solvent was removed under reduced pressure
  4. additionthe residue was treated with 2N NaOH (15 ml)
  5. extractionextracted with ethyl acetate (20 ml)
  6. washthe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customto give a residue that
  11. filtrationfiltered
  12. customdried at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-c5cf0deaedee4f9ba2d1c4a538430c1a
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07220769B2

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