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

HRID 1178584노트

반응식

HRID 1178584 반응식
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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0816b81333f34ffbbfc2d4c8153b9f26
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276527B2

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