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

HRID 6878

Reaction equation

HRID 6878 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 220190546-(5-Formyl-thiazol-2-ylamino)-nicotinic acidYield 96.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b1ddbc472b3f4e66b63e1ab615f44a28
Source dataset
uspto-grants-2006_08
Patent number
US07084160B2

Linked notes

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