2,3-Diaminobenzoic acid → 2-(2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yloxy)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid

HRID 85116

Reaktionsgleichung

Reaktionsgleichung von HRID 85116
[NH2:1][C:2]1[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:12]([C:14]1[CH:32]=[CH:31][CH:30]=[CH:29][C:15]=1[O:16][CH:17]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18]1)=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C.O>[C:25]([O:24][C:22]([N:19]1[CH2:20][CH2:21][CH:17]([O:16][C:15]2[CH:29]=[CH:30][CH:31]=[CH:32][C:14]=2[C:12]2[NH:11][C:10]3[CH:9]=[CH:8][CH:7]=[C:3]([C:4]([OH:6])=[O:5])[C:2]=3[N:1]=2)[CH2:18]1)=[O:23])([CH3:28])([CH3:27])[CH3:26]

Komponenten

6

Edukt 3

HCID 1980692,3-Diaminobenzoic acidHCID 656671Sodium PyrosulfiteHCID 58278994HCID 58278994, Verbindung

Produkt 1

HCID 672015052-(2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yloxy)phenyl)-1H-benzo[d]imidazole-4-carboxylic acidAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 2,3-diaminobenzoic acid (1; 350 mg, 2.3 mmol), tert-butyl 3-(2-formylphenoxy)pyrrolidine-1-carboxylate (30; 670 mg, 2.3 mmol) and Na2S2O5 (568 mg, 1.3 mmol) in DMF (30 mL) was stirred at 90° C. for 18 h. The mixture was cooled to room temperature. The mixture was diluted with water (100 mL), stirred for 1 h, filtered, and washed with water. The filter cake was dried under vacuum to afford 822 mg of the titled compound 31 (84%). MS (ESI) calcd for C23H25N3O5: 423.18; found: 424 [M+H].

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. stirringstirred for 1 h
  3. filtrationfiltered
  4. washwashed with water
  5. customThe filter cake was dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-37d62cfde9ea40d0ad2db6e3cbb76086
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846947B2

Verknüpfte Notizen

Wird geladen…