Triethylamine → N-[4-[2-Amino-4-(4-methoxyphenyl)-1,3-thiazol-5-YL]-2-pyridyl]benzamide

HRID 1178590ノート

反応式

HRID 1178590 の反応式
BrBr.[C:3]([NH:11][C:12]1[CH:17]=[C:16]([CH2:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=O)[CH:15]=[CH:14][N:13]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:29][C:30]([NH2:32])=[S:31].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(O)(=O)C>[NH2:32][C:30]1[S:31][C:18]([C:16]2[CH:15]=[CH:14][N:13]=[C:12]([NH:11][C:3](=[O:10])[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:17]=2)=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[N:29]=1

参加物

7

反応物 5

HCID 8471TriethylamineHCID 24408BromineHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 219642602-(2-Benzoylamino-4-pyridyl)-1-(4-methoxyphenyl)ethanone

生成物 1

HCID 9865835N-[4-[2-Amino-4-(4-methoxyphenyl)-1,3-thiazol-5-YL]-2-pyridyl]benzamide収率 21%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

Bromine (0.11 mL, 2.1 mmol) was added to a solution of 2-(2-benzoylamino-4-pyridyl)-1-(4-methoxyphenyl)ethanone (0.72 g, 2.1 mmol) in acetic acid (20 mL) at 0° C. and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated. The residue was dissolved in acetonitrile. (20 mL), to the solution were added thiourea (0.17 g, 2.2 mmol) and triethylamine (0.35 mL, 2.5 mmol) and the mixture was stirred at 80° C. for 5 hours. After the reaction mixture was cooled to room temperature, a saturated aqueous solution of sodium hydrogencarbonate (200 mL) was added and the resulting solid was filtered and washed with water. The resulting crude crystals were collected by filtration and washed with water. The crude crystals were recrystallized from ethanol to obtain 0.17 g (0.43 mmol, yield 21%) of the title compound.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in acetonitrile
  3. stirringthe mixture was stirred at 80° C. for 5 hours
  4. temperatureAfter the reaction mixture was cooled to room temperature
  5. filtrationthe resulting solid was filtered
  6. washwashed with water
  7. filtrationThe resulting crude crystals were collected by filtration
  8. washwashed with water
  9. customThe crude crystals were recrystallized from ethanol

出典と根拠

ORDレコード
ord-88270bfa52ac4d1daf57b8735f15dd40
出典データセット
uspto-grants-2007_10
特許番号
US07276527B2

反応ノート

読み込み中…