2-Bromopropanedial → 6-(5-Formyl-thiazol-2-ylamino)-nicotinic acid

HRID 6878

Reaktionsgleichung

Reaktionsgleichung von HRID 6878
[NH:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][N:6]=1)[C:2]([NH2:4])=[S:3].Br[CH:15]([CH:18]=O)[CH:16]=[O:17].C([O-])(=O)C.[Na+]>C(O)(=O)C.O>[CH:16]([C:15]1[S:3][C:2]([NH:1][C:5]2[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][N:6]=2)=[N:4][CH:18]=1)=[O:17]

Komponenten

6

Edukt 3

HCID 749452-BromopropanedialHCID 517045Sodium AcetateHCID 220190936-(Carbamothioylamino)pyridine-3-carboxylic acid

Produkt 1

HCID 220190546-(5-Formyl-thiazol-2-ylamino)-nicotinic acidAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 6-thioureido-nicotinic acid (197 mg, 1 mmol), 2-bromomalonaldehyde (166 mg, 1.1 mmol) and sodium acetate (100 mg) in acetic acid (2 mL) was stirred at 100° C. for 20 min. The mixture was then cooled to RT, diluted with water and the precipitates were collected. The solid was washed with water, then methanol and dried in vacuo to afford 6-(5-formyl-thiazol-2-ylamino)-nicotinic acid, (240 mg, 96%). MS m/z 250 (M+H)+. 1H NMR (DMSO-d6) δ 12.7 (s, 1 H), 9.12 (s, 1 H), 8.92 (s, 1 H), 8.38 (s, 1 H), 8.24 (d, 1 H, J=5.6 Hz), 7.21 (d, 1 H, J=5.6 Hz). 13C NMR (DMSO-d6) δ 183.5, 166.0, 165.1, 153.3, 151.5, 148.8, 139.1, 131.2, 120.3, 110.0.

Aufarbeitung

  1. temperatureThe mixture was then cooled to RT
  2. customthe precipitates were collected
  3. washThe solid was washed with water
  4. dry with materialmethanol and dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b1ddbc472b3f4e66b63e1ab615f44a28
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084160B2

Verknüpfte Notizen

Wird geladen…