3-Pyridinecarbonyl chloride, hydrochloride (1:1) → N-[5-(2-benzylamino-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]nicotinamide

HRID 1268738ノート

反応式

HRID 1268738 の反応式
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([C:15]2[S:19][C:18]([NH2:20])=[N:17][C:16]=2[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=2)[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[N:32][CH:31]=1.C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([C:15]2[S:19][C:18]([NH:20][C:29](=[O:36])[C:30]3[CH:35]=[CH:34][CH:33]=[N:32][CH:31]=3)=[N:17][C:16]=2[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=2)[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 21964259[5-(2-Benzylamino-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amine

生成物 1

HCID 10277320N-[5-(2-benzylamino-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]nicotinamide収率 59%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of [5-(2-benzylamino-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amine (0.52 g, 1.4 mmol) and 4-dimethylaminopyridine (0.051 g, 0.42 mmol) in N,N-dimethylacetamide (10 mL) was added nicotinoyl chloride hydrochloride (0.37 g, 2.1 mmol), and the mixture was stirred at 80° C. for 14 hrs. Into the reaction mixture was poured aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated. The resulting crystals were crystallized from isopropyl ether to give the title compound (0.28 g, yield 59%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customThe resulting crystals were crystallized from isopropyl ether

出典と根拠

ORDレコード
ord-f2a3c9a36a554606a942924f1085e649
出典データセット
uspto-grants-2007_04
特許番号
US07199124B2

反応ノート

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