Pyridine → 2-(4-pyridin-3-yl-1,3-thiazol-2-yl)-1H-benzimidazole-4-carboxamide

HRID 564216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 564216
N1C=CC=[C:3]([C:7]2[S:8][CH:9]=[C:10](C(O)=O)[N:11]=2)C=1.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.Cl.[NH2:29][C:30]1[C:38]([NH2:39])=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([NH2:34])=[O:33].[N:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CN(C=O)C>[N:40]1[CH:45]=[CH:44][CH:43]=[C:42]([C:10]2[N:11]=[C:7]([C:3]3[NH:39][C:38]4[CH:37]=[CH:36][CH:35]=[C:31]([C:32]([NH2:34])=[O:33])[C:30]=4[N:29]=3)[S:8][CH:9]=2)[CH:41]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 682631,1'-CarbonyldiimidazoleHCID 7365132-(3-Pyridyl)thiazole-4-carboxylic acidHCID 534228072,3-Diaminobenzamide dihydrochloride

Produkt 1

HCID 1363466312-(4-pyridin-3-yl-1,3-thiazol-2-yl)-1H-benzimidazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a mixture of 2-(3-pyridyl)-1,3-thiazole-4-carboxylic acid (300 mg) in pyridine (5 mL) and DMF (5 mL) at ambient temperature was added CDI (248 mg). The mixture was heated at 40° C. for 2 hours, treated with 2,3-diaminobenzamide dihydrochloride (326 mg), stirred at ambient temperature for 16 hours and concentrated. The concentrate was heated in glacial acetic acid (20 mL) at 110° C. for 2 hours, cooled and concentrated. The concentrate was partitioned between ethyl acetate and sodium bicarbonate solution, and the solid that precipitated was filtered and washed with water and ethyl acetate. 1H NMR (DMSO-d6) δ 7.38 (t, J=7.8 Hz, 1H), 7.60-7.67 (m, 1H), 7.78 (d, J=7.8 Hz, 1H), 7.81 (brs, 1H), 7.90 (dd, J=7.46, 1.0 Hz, 1H), 8.44-8.50 (m, 1H), 8.74-8.76 (m, 1H), 8.74 (s, 1H), 9.29 (brs, 1H), 9.34 (d, J=1.7 Hz, 1H), 13.44 (brs, 1H).

Aufarbeitung

  1. concentrationconcentrated
  2. temperatureThe concentrate was heated in glacial acetic acid (20 mL) at 110° C. for 2 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. customThe concentrate was partitioned between ethyl acetate and sodium bicarbonate solution
  6. customthe solid that precipitated
  7. filtrationwas filtered
  8. washwashed with water and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-6b31889c129843c59b098b6eaacdf351
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067613B2

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