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Triphenylphosphine → 3-[(4-Methoxyphenyl)amino]-1-[(5-methylisoxazol-3-yl)methyl]-4-phenyl-1H-pyrrole-2,5-dione

HRID 2113770
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HRID 2113770 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:11](=[O:22])[NH:12][C:13](=[O:21])[C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.[CH3:23][C:24]1[O:28][N:27]=[C:26]([CH2:29]O)[CH:25]=1.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]2[C:11](=[O:22])[N:12]([CH2:29][C:26]3[CH:25]=[C:24]([CH3:23])[O:28][N:27]=3)[C:13](=[O:21])[C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][CH:8]=1
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6

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HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2736567(5-Methyl-1,2-oxazol-3-yl)methanolHCID 691437143-[(4-methoxyphenyl)amino]-4-phenyl-1H-pyrrole-2,5-dione

생성물 1

HCID 113726913-[(4-Methoxyphenyl)amino]-1-[(5-methylisoxazol-3-yl)methyl]-4-phenyl-1H-pyrrole-2,5-dione수율 21.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
130 °C

실험 절차

To a solution of 3-[(4-methoxyphenyl)amino]-4-phenyl-1H-pyrrole-2,5-dione (0.17 mmol, 50 mg), 5-methylisoxazole-3-methanol (0.19 mmol, 21 mg) and diethyl azodicarboxylate (0.19 mmol, 33 mg) in dry THF (1 mL) was added triphenylphosphine (0.19 mmol, 49 mg) in dry THF (1 mL). The mixture was heated in a microwave reactor at 130° C. for six min. After cooling, the reaction mixture was purified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN) to give 14 mg (21%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 7.23 (bs, 1H), 7.16-7.06 (m, 3H), 7.01-6.96 (m, 2H), 6.63-6.53 (m, 4H), 6.03 (d, J=0.7 Hz, 1H), 4.82 (s, 2H), 3.70 (s, 3H), 2.39 (d, J=0.7 Hz, 3H).

후처리

  1. temperatureAfter cooling
  2. customthe reaction mixture was purified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN)

출처 및 근거

ORD 기록
ord-1ee0ba7a571e4eba96b96934a218d55b
출처 데이터셋
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07432288B2

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