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Phenylacetyl isothiocyanate → Morpholine-4-carboxylic acid {4-[2-fluoro-4-(3-phenylacetylthioureido)phenoxy]pyridin-2-yl}amide

HRID 492783
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HRID 492783 반응식
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[O:15])[CH:8]=2)=[C:4]([F:24])[CH:3]=1.[C:25]1([CH2:31][C:32]([N:34]=[C:35]=[S:36])=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C=O.C(OCC)C>[F:24][C:4]1[CH:3]=[C:2]([NH:1][C:35]([NH:34][C:32](=[O:33])[CH2:31][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[S:36])[CH:23]=[CH:22][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)=[O:15])[CH:8]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 12454157Phenylacetyl isothiocyanateHCID 57677752N-(4-(4-amino-2-fluorophenoxy)pyridin-2-yl)morpholine-4-carboxamide

생성물 1

HCID 57677431Morpholine-4-carboxylic acid {4-[2-fluoro-4-(3-phenylacetylthioureido)phenoxy]pyridin-2-yl}amide수율 29%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide
용매

실험 절차

To a solution of morpholine-4-carboxylic acid [4-(4-amino-2-fluorophenoxy)pyridin-2-yl]amide (50 mg) in N,N-dimethylformamide (1.0 ml) was added phenylacetyl isothiocyanate (42 mg), followed by stirring at room temperature for 22 hrs. The reaction mixture was partitioned between ethyl acetate and water. 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; hexane:ethyl acetate=1:1, ethyl acetate, then ethyl acetate:methanol=10:1). Fractions containing the target compound were concentrated to give a solid, which was suspended in diethyl ether. The solid was filtered off, washed with diethyl ether, and dried under aeration to provide the titled compound (22 mg, 0.043 mmol, 29%) as colorless solid.

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customto give a residue, which
  6. customwas then purified by silica gel column chromatography (eluent
  7. additionFractions containing the target compound
  8. concentrationwere concentrated
  9. customto give a solid, which
  10. filtrationThe solid was filtered off
  11. washwashed with diethyl ether
  12. customdried under aeration

출처 및 근거

ORD 기록
ord-f97e70a760fc4879abdcfc8afe8d1fd3
출처 데이터셋
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07531532B2

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