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Diisopropylethylamine → 3-{4-Fluoro-3-[(5-phenyl-furan-2-carbonyl)-amino]-phenyl}-acrylic acid methyl ester

HRID 659119
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HRID 659119 반응식
[C:1]1([C:7]2[O:11][C:10]([C:12]([OH:14])=O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][O:16][C:17](=[O:28])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[C:22]([NH2:27])[CH:21]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH3:15][O:16][C:17](=[O:28])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[C:22]([NH:27][C:12]([C:10]2[O:11][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][CH:9]=2)=[O:14])[CH:21]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 7362555-Phenylfuran-2-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 684148563-(3-Amino-4-fluoro-phenyl)-acrylic acid methyl ester

생성물 1

HCID 684122363-{4-Fluoro-3-[(5-phenyl-furan-2-carbonyl)-amino]-phenyl}-acrylic acid methyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5-phenyl-2-furoic acid (36) (18 mg, 0.15 mmol) was coupled to aniline (43) (30 mg, 0.15 mmol) using Method B, except that DIPEA (40 mg, 0.31 mmol) and DMF (2 mL) were used and the reaction was stirred at ambient temperature for 2.5 hours, then at 40° C. for 24 hours. Further TBTU (1 eq) and acid (1 eq) were added and the reaction heated at 60° C. for a further 6 hours to give the crude title compound after work-up. The residue was purified using column chromatography eluting with 20% EtOAc in heptane to give the title compound. Yield: 18 mg, 32%; LC-MS tr 1.55 min; HPLC Purity: 83%; MS (ES+) m/z 366 (M+H)

후처리

  1. waitat 40° C. for 24 hours
  2. temperaturethe reaction heated at 60° C. for a further 6 hours
  3. customto give the crude title compound after work-up
  4. customThe residue was purified
  5. washeluting with 20% EtOAc in heptane

출처 및 근거

ORD 기록
ord-7b9f03991b584eac8f90f41084015ef1
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08080567B2

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