1,1'-Carbonyldiimidazole → (r)-Tert-butyl 2-(5-(4-carbamoyl-1h-benzimidazol-2-yl)thiophen-2-yl)pyrrolidine-1-carboxylate

HRID 564221Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 564221
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]1[S:14][C:15]([C:18](O)=O)=[CH:16][CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.Cl.[NH2:35][C:36]1[C:44]([NH2:45])=[CH:43][CH:42]=[CH:41][C:37]=1[C:38]([NH2:40])=[O:39]>N1C=CC=CC=1.CN(C=O)C>[C:38]([C:37]1[C:36]2[N:35]=[C:18]([C:15]3[S:14][C:13]([C@H:9]4[CH2:10][CH2:11][CH2:12][N:8]4[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:17][CH:16]=3)[NH:45][C:44]=2[CH:43]=[CH:42][CH:41]=1)(=[O:39])[NH2:40]

Komponenten

6

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 534228072,3-Diaminobenzamide dihydrochlorideHCID 66759425(r)-2-(5-Carboxythiophen-2-yl)pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 66760174(r)-Tert-butyl 2-(5-(4-carbamoyl-1h-benzimidazol-2-yl)thiophen-2-yl)pyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of EXAMPLE 16B (2.4 g) in pyridine (20 mL) and DMF (20 mL) was added CDI (1.6 g), and the mixture was stirred at 40° C. for 1 hour. 2,3-Diaminobenzamide dihydrochloride (1.8 g) was added, and the mixture stirred at ambient temperature overnight and concentrated. The concentrate was stirred in of acetic acid (20 mL) at 80° C. for 4 hours and concentrated. The concentrate was partitioned between ethyl acetate and saturated sodium bicarbonate solution, and the extract was washed with water and concentrated. The concentrate was purified by flash chromatography on silica gel with 40-80% ethyl acetate in hexane.

Aufarbeitung

  1. stirringthe mixture stirred at ambient temperature overnight
  2. concentrationconcentrated
  3. stirringThe concentrate was stirred in of acetic acid (20 mL) at 80° C. for 4 hours
  4. concentrationconcentrated
  5. customThe concentrate was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  6. washthe extract was washed with water
  7. concentrationconcentrated
  8. customThe concentrate was purified by flash chromatography on silica gel with 40-80% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-dca1c0030b2c457ebd754654f2b7a5dc
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067613B2

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