Triphenylphosphine → methyl (E)-3-(2-{3-[6-oxo-3-(3,4,5-trifluorophenyl)-6H-pyridazin-1-ylmethyl]phenyl}pyrimidin-5-yl)acrylate

HRID 1408397노트

반응식

HRID 1408397 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[CH:12][C:13](=[O:16])[NH:14][N:15]=2)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].O[CH2:18][C:19]1[CH:20]=[C:21]([C:25]2[N:30]=[CH:29][C:28](/[CH:31]=[CH:32]/[C:33]([O:35][CH3:36])=[O:34])=[CH:27][N:26]=2)[CH:22]=[CH:23][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[O:16]=[C:13]1[N:14]([CH2:18][C:19]2[CH:20]=[C:21]([C:25]3[N:26]=[CH:27][C:28](/[CH:31]=[CH:32]/[C:33]([O:35][CH3:36])=[O:34])=[CH:29][N:30]=3)[CH:22]=[CH:23][CH:24]=2)[N:15]=[C:10]([C:4]2[CH:5]=[C:6]([F:9])[C:7]([F:8])=[C:2]([F:1])[CH:3]=2)[CH:11]=[CH:12]1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58289762methyl (E)-3-[2-(3-hydroxymethylphenyl)pyrimidin-5-yl]acrylateHCID 594068096-(3,4,5-trifluorophenyl)-2H-pyridazin-3-one

생성물 1

HCID 59484916methyl (E)-3-(2-{3-[6-oxo-3-(3,4,5-trifluorophenyl)-6H-pyridazin-1-ylmethyl]phenyl}pyrimidin-5-yl)acrylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

47.2 90 mg (0.4 mmol) of 6-(3,4,5-trifluorophenyl)-2H-pyridazin-3-one and 111 mg (0.41 mmol) of methyl (E)-3-[2-(3-hydroxymethylphenyl)-pyrimidin-5-yl]acrylate are suspended in 3 ml of THF with 200 mg (0.6 mmol) of polymer-bound triphenylphosphine (about 3 mmol of triphenylphosphine per g), and the mixture is shaken at room temperature for 30 min. The mixture is cooled to 0° C., and 95 μl (0.6 mmol) of diethyl azodicarboxylate are added. The reaction mixture is shaken at room temperature for 24 h. The reaction mixture is purified by means of preparative HPLC; yield: 7 mg of “A283”; HPLC: Rt=3.41 min (method C);

후처리

  1. temperatureThe mixture is cooled to 0° C.
  2. stirringThe reaction mixture is shaken at room temperature for 24 h
  3. customThe reaction mixture is purified by means of preparative HPLC

출처 및 근거

ORD 기록
ord-85d8995e7a5043998b0aa0553126da58
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921357B2

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