Phenylacetyl chloride → 2-Amino-4-{3-methoxy-4-[3-(2-phenylacetyl)thioureido]phenoxy}pyridine

HRID 492713노트

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HRID 492713 반응식
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S-:11][C:12]#[N:13].[K+].[NH2:15][C:16]1[CH:21]=[C:20]([O:22][C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[C:25]([O:30][CH3:31])[CH:24]=2)[CH:19]=[CH:18][N:17]=1>C(#N)C>[NH2:15][C:16]1[CH:21]=[C:20]([O:22][C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:12]([NH:13][C:8](=[O:9])[CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[S:11])=[C:25]([O:30][CH3:31])[CH:24]=2)[CH:19]=[CH:18][N:17]=1

참가 물질

5

반응물 3

HCID 7679Phenylacetyl chlorideHCID 516872Potassium thiocyanateHCID 231532722-Amino-4-(4-amino-3-methoxyphenoxy)pyridine

생성물 1

HCID 576777282-Amino-4-{3-methoxy-4-[3-(2-phenylacetyl)thioureido]phenoxy}pyridine수율 39%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

2-Phenylacetyl chloride (0.198 ml) was dissolved in acetonitrile (10 ml) under a nitrogen atmosphere, and then potassium thiocyanate (292 mg) was added at 60° C., followed by stirring at the same temperature for 3.5 hrs. The reaction mixture was cooled down to room temperature, and then 2-amino-4-(4-amino-3-methoxyphenoxy)pyridine (231.3 mg) was added thereto, followed by further stirring for 2 hrs. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was washed with water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (eluent; ethyl acetate, then ethyl acetate:methanol=9:1) to provide the titled compound (158 mg, 39%) as pale brown powder.

후처리

  1. stirringby further stirring for 2 hrs
  2. customThe reaction mixture was partitioned between ethyl acetate
  3. washThe organic layer was washed with water and brine in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under a reduced pressure
  6. customto give a residue, which
  7. customwas then purified by silica gel column chromatography (eluent

출처 및 근거

ORD 기록
ord-8af9d4ffcef348eeb558b025571d161c
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531532B2

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