Diisopropylethylamine → 6-Methoxy-N-(3-(pyridin-3-yloxy)phenyl)picolinamide

HRID 1887438노트

반응식

HRID 1887438 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=2)[NH2:11])[CH:2]=1.[CH3:15][O:16][C:17]1[N:22]=[C:21]([C:23](O)=[O:24])[CH:20]=[CH:19][CH:18]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C>C(Cl)Cl.O>[CH3:15][O:16][C:17]1[N:22]=[C:21]([C:23]([NH:11][C:10]2[CH:12]=[CH:13][CH:14]=[C:8]([O:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:9]=2)=[O:24])[CH:20]=[CH:19][CH:18]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 5708916-Methoxypicolinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 212855823-(Pyridin-3-yloxy)aniline

생성물 1

HCID 583375646-Methoxy-N-(3-(pyridin-3-yloxy)phenyl)picolinamide수율 93.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

Compound 5 (25 mg, 0.13 mmol, 1.0 eq), 6-methoxypicolinic acid (23 mg, 0.15 mmol, 1.1 eq), 2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (56 mg, 0.15 mmol, 1.1 eq) and DIEA (25.7 μL, 0.148 mmol, 1.10 eq) were dissolved in CH2Cl2 (1.5 mL) and stirred at rt overnight. Water was added and the layers separated. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 39 mg (90%) of the title compound as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 10.26 (s, 1H), 8.41 (d, J=2.5 Hz, 1H), 8.38 (dd, J=4.4, 1.5 Hz, 1H), 7.92 (t, J=7.8 Hz, 1H), 7.70-7.69 (m, 2H), 7.65 (d, J=8.6 Hz, 1H), 7.48 (ddd, J=8.4, 2.7, 1.6 Hz, 1H), 7.45-7.39 (m, 2H), 7.08 (d, J=8.0 Hz, 1H), 6.84 (dd, J=8.1, 1.9 Hz, 1H), 4.04 (s, 3H); ES-MS [M+1]+: 322.2.

후처리

  1. customthe layers separated
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-4985e670b37340e59ac516f19ac68d39
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501757B2

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