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

HRID 6878

반응식

HRID 6878 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b1ddbc472b3f4e66b63e1ab615f44a28
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084160B2

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