2-Aminothiazole → 2-(2-(piperidin-4-yloxy)phenyl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide

HRID 85113

Reaktionsgleichung

Reaktionsgleichung von HRID 85113
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]2[NH:25][C:24]3[CH:26]=[CH:27][CH:28]=[C:29]([C:30](O)=[O:31])[C:23]=3[N:22]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[S:33]1[CH:37]=[CH:36][N:35]=[C:34]1[NH2:38].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]2[NH:25][C:24]3[CH:26]=[CH:27][CH:28]=[C:29]([C:30]([NH:38][C:34]4[S:33][CH:37]=[CH:36][N:35]=4)=[O:31])[C:23]=3[N:22]=2)[CH2:10][CH2:9]1

Komponenten

5

Edukt 3

HCID 21552-AminothiazoleHCID 6422Trifluoroacetic acidHCID 672032822-(2-(1-(tert-butoxycarbonyl)piperidin-4-yloxy)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid

Produkt 1

HCID 866537892-(2-(piperidin-4-yloxy)phenyl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The same general amide coupling procedure outlined above was used, employing 2-(2-(1-(tert-butoxycarbonyl)piperidin-4-yloxy)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid 27 and 2-aminothiazole 4 as the starting materials. The resulting crude amide coupling product (0.2 mmol) was treated with 4 mL of 25% TFA in CH2Cl2 and allowed to stand at room temperature for 8 h. The mixture was concentrated under reduced pressure and the resulting residue was purified by preparative HPLC using aqueous acetonitrile that has buffered with 0.1% TFA to afford 2-(2-(piperidin-4-yloxy)phenyl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide (Compound 428). MS (ESI) calcd for C22H21N5O2S: 419.14; found: 420 [M+H].

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-541473204a8843828113408da152ec4a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846947B2

Verknüpfte Notizen

Wird geladen…