Diisopropylethylamine → N-{4-[2-Amino-5-(3,4-dimethoxyphenyl)pyridin-3-yl]phenyl}-5-(4-fluorophenyl)-4-oxo-1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1,4-dihydropyridine-3-carboxamide

HRID 1428083노트

반응식

HRID 1428083 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:26])[C:10]([C:23]([OH:25])=O)=[CH:11][N:12]([CH2:14][CH2:15][O:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[CH:13]=2)=[CH:4][CH:3]=1.C1C=NC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:70][C:71]1[CH:76]=[CH:75][C:74]([C:77]2[C:78]([NH2:93])=[N:79][CH:80]=[C:81]([C:83]3[CH:88]=[CH:87][C:86]([O:89][CH3:90])=[C:85]([O:91][CH3:92])[CH:84]=3)[CH:82]=2)=[CH:73][CH:72]=1>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[NH2:93][C:78]1[C:77]([C:74]2[CH:73]=[CH:72][C:71]([NH:70][C:23]([C:10]3[C:9](=[O:26])[C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)=[CH:13][N:12]([CH2:14][CH2:15][O:16][CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][O:18]4)[CH:11]=3)=[O:25])=[CH:76][CH:75]=2)=[CH:82][C:81]([C:83]2[CH:88]=[CH:87][C:86]([O:89][CH3:90])=[C:85]([O:91][CH3:92])[CH:84]=2)=[CH:80][N:79]=1

참가 물질

9

반응물 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86700031HCID 86700031, 화합물HCID 867000345-(4-Fluorophenyl)-4-oxo-1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1,4-dihydropyridine-3-carboxylic acid

생성물 1

HCID 86700033N-{4-[2-Amino-5-(3,4-dimethoxyphenyl)pyridin-3-yl]phenyl}-5-(4-fluorophenyl)-4-oxo-1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1,4-dihydropyridine-3-carboxamide

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

5-(4-Fluorophenyl)-4-oxo-1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1,4-dihydropyridine-3-carboxylic acid was dissolved in DMF (2 ml), and HOAt (41 mg), HATU (170 mg), DMAP (18 mg) and DIPEA (88 μl) were added at room temperature. The reaction mixture was stirred at room temperature for three hours. The compound obtained in Step 2 of Example 1 (96 mg) was added to the reaction mixture at room temperature, followed by stirring overnight. Water was added to the reaction mixture, and the precipitated solid was collected by filtration to give 281 mg of the crude purified title compound as a solid. One hundred forty one mg of the solid was purified by PLC [dichloromethane:methanol=20:1 (v/v)], and the eluate was concentrated under reduced pressure. The residue was purified by PLC [ethyl acetate:methanol=15:1 (v/v)] to give 72 mg of the title compound.

후처리

  1. stirringby stirring overnight
  2. filtrationthe precipitated solid was collected by filtration
  3. customto give 281 mg of the crude
  4. custompurified title compound as a solid
  5. customOne hundred forty one mg of the solid was purified by PLC [dichloromethane:methanol=20:1 (v/v)]
  6. concentrationthe eluate was concentrated under reduced pressure
  7. customThe residue was purified by PLC [ethyl acetate:methanol=15:1 (v/v)]

출처 및 근거

ORD 기록
ord-6f356b773e8e4309922bce43fd656b1c
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933103B2

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