Triethylamine → [5-(2-Fluoro-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amine

HRID 1178584ノート

反応式

HRID 1178584 の反応式
BrBr.[F:3][C:4]1[CH:9]=[C:8]([CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)=O)[CH:7]=[CH:6][N:5]=1.C(N(CC)CC)C.[NH2:27][C:28]([NH2:30])=[S:29].C(=O)([O-])O.[Na+]>C(O)(=O)C.C(#N)C>[F:3][C:4]1[CH:9]=[C:8]([C:10]2[S:29][C:28]([NH2:30])=[N:27][C:11]=2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)[CH:7]=[CH:6][N:5]=1

参加物

8

反応物 5

HCID 8471TriethylamineHCID 24408BromineHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 115431572-(2-Fluoro-4-pyridyl)-1-(3-methylphenyl)ethanone

生成物 1

HCID 9878963[5-(2-Fluoro-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amine収率 35%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6342Acetonitrile溶媒

実験手順

Bromine (1.9 mL, 37 mmol) was added to a solution of 2-(2-fluoro-4-pyridyl)-1-(3-methylphenyl)ethanone (8.5 g, 37 mmol) in acetic acid (50 mL) and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated. Triethylamine (5.2 mL, 37 mmol) was added to a mixture of this residue and thiourea (3.0 g, 40 mmol) in acetonitrile (50 mL) and the mixture was stirred at 80° C. for 2 hours. A saturated aqueous solution of sodium hydrogencarbonate (50 mL) was added to the reaction mixture and the precipitated solid was collected by filtration. After the resulting solid was washed with water, it was dried. The crude crystals were recrystallized from ethanol to obtain 3.7 g (yield 35%) of the title compound.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. stirringthe mixture was stirred at 80° C. for 2 hours
  3. filtrationthe precipitated solid was collected by filtration
  4. washAfter the resulting solid was washed with water, it
  5. customwas dried
  6. customThe crude crystals were recrystallized from ethanol

出典と根拠

ORDレコード
ord-0816b81333f34ffbbfc2d4c8153b9f26
出典データセット
uspto-grants-2007_10
特許番号
US07276527B2

反応ノート

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