1,1-dimethylethyl 4-[7-(aminocarbonyl)-5-(2-thienyl)-1H-indol-3-yl]-1-piperidinecarboxylate → 3-(4-piperidinyl)-5-(2-thienyl)-1H-indole-7-carboxamide

HRID 2267488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2267488
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([C:26]2[S:27][CH:28]=[CH:29][CH:30]=2)[CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[C:9]2[CH:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1)=[O:3]>CO.Cl>[NH:16]1[CH2:17][CH2:18][CH:13]([C:9]2[C:8]3[C:12](=[C:4]([C:2]([NH2:1])=[O:3])[CH:5]=[C:6]([C:26]4[S:27][CH:28]=[CH:29][CH:30]=4)[CH:7]=3)[NH:11][CH:10]=2)[CH2:14][CH2:15]1

Komponenten

4

Edukt 1

HCID 596006591,1-dimethylethyl 4-[7-(aminocarbonyl)-5-(2-thienyl)-1H-indol-3-yl]-1-piperidinecarboxylate

Produkt 1

HCID 596006613-(4-piperidinyl)-5-(2-thienyl)-1H-indole-7-carboxamideAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1,1-dimethylethyl 4-[7-(aminocarbonyl)-5-(2-thienyl)-1H-indol-3-yl]-1-piperidinecarboxylate (90 mg, 0.22 mmol) in MeOH (3 mL), HCl (4.0M in dioxane, 2.06 mL) was added. The reaction mixture was stirred at ambient temperature for 2 hours, after which time the solvent was removed under reduced pressure and the resulting residue was partitioned between ethyl acetate (10 mL) and 10% sodium hydroxide (10 mL). The aqueous layer was extracted with ethyl acetate (10 mL×2) and the combined organic phase was dried over MgSO4 and concentrated to give a crude product (53 mg, 77%). This was used directly in the next step without further purification.

Aufarbeitung

  1. customafter which time the solvent was removed under reduced pressure
  2. customthe resulting residue was partitioned between ethyl acetate (10 mL) and 10% sodium hydroxide (10 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (10 mL×2)
  4. dry with materialthe combined organic phase was dried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ec7eb6e510f64a999f7f266b95d0a5e2
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858796B2

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