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

HRID 1985762

反応式

HRID 1985762 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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, 1H), 9.12 (s, 1H), 8.92 (s, 1H), 8.38 (s, 1H), 8.24 (d, 1H, J=5.6 Hz), 7.21 (d, 1H, 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.

後処理

  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

出典と根拠

ORDレコード
ord-2c4b374d3f0f43d587f06df6c0e52c6a
出典データセット
uspto-grants-2009_06
特許番号
US07547711B2

関連ノート

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