Phenylacetyl chloride → Pyrrolidine-1-carboxylic acid {4-[2-methyl-4-(3-phenylacetylthioureido)phenoxy]pyridin-2-yl}amide

HRID 492787노트

반응식

HRID 492787 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:36]=[CH:35][C:19]([O:20][C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]([N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[O:29])[CH:22]=2)=[C:18]([CH3:37])[CH:17]=1>C(#N)C.C(OCC)C>[CH3:37][C:18]1[CH:17]=[C:16]([NH:15][C:12]([NH:13][C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[S:11])[CH:36]=[CH:35][C:19]=1[O:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]([N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:29])[CH:22]=1

참가 물질

6

반응물 3

HCID 7679Phenylacetyl chlorideHCID 516872Potassium thiocyanateHCID 57677322Pyrrolidine-1-carboxylic acid [4-(4-amino-2-methylphenoxy)pyridin-2-yl]amide

생성물 1

HCID 57677434Pyrrolidine-1-carboxylic acid {4-[2-methyl-4-(3-phenylacetylthioureido)phenoxy]pyridin-2-yl}amide수율 41%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

To a solution of 2-phenylacetyl chloride (0.0549 ml) in acetonitrile (5.0 ml) was added potassium thiocyanate (37.3 mg, 0.384 mmol), followed by stirring under a nitrogen atmosphere at 50° C. for 1 hr. The reaction mixture was cooled down to room temperature, and then pyrrolidine-1-carboxylic acid [4-(4-amino-2-methylphenoxy)pyridin-2-yl]amide (80 mg) was added thereto, followed by stirring under a nitrogen atmosphere for 21 hrs. The reaction mixture was partitioned between ethyl acetate (100 ml) and water (40 ml). The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then purified by silica gel column chromatography (eluent; ethyl acetate). Fractions containing the target compound were concentrated to give a solid, which was suspended in diethyl ether (4 ml). The solid was filtered off, and dried under aeration to provide the titled compound (51 mg, 41%) as colorless powder.

후처리

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. stirringby stirring under a nitrogen atmosphere for 21 hrs
  3. customThe reaction mixture was partitioned between ethyl acetate (100 ml) and water (40 ml)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customto give a residue, which
  8. customwas then purified by silica gel column chromatography (eluent; ethyl acetate)
  9. additionFractions containing the target compound
  10. concentrationwere concentrated
  11. customto give a solid, which
  12. filtrationThe solid was filtered off
  13. customdried under aeration

출처 및 근거

ORD 기록
ord-787e6be1d5c64d22b674b350b006b9d9
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531532B2

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