2,6-Lutidine → N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-(4-pyridin-3-yl-[1,2,3]triazol-1-yl)-benzamide

HRID 2109174노트

반응식

HRID 2109174 반응식
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N:11]1[CH:15]=[C:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[N:13]=[N:12]1.C(Cl)(=O)C(Cl)=O.[NH2:28][C:29]1[C:30]([O:44][CH3:45])=[C:31]([NH:39][S:40]([CH3:43])(=[O:42])=[O:41])[CH:32]=[C:33]([C:35]([CH3:38])([CH3:37])[CH3:36])[CH:34]=1.N1C(C)=CC=CC=1C>C(Cl)Cl.CN(C=O)C.C1COCC1>[C:35]([C:33]1[CH:32]=[C:31]([NH:39][S:40]([CH3:43])(=[O:42])=[O:41])[C:30]([O:44][CH3:45])=[C:29]([NH:28][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([N:11]3[CH:15]=[C:14]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)[N:13]=[N:12]3)[CH:4]=2)[CH:34]=1)([CH3:38])([CH3:36])[CH3:37]

참가 물질

8

반응물 4

HCID 79372,6-LutidineHCID 65578Oxalyl chlorideHCID 10214710N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamideHCID 210973314-Methyl-3-(4-pyridin-3-yl-1,2,3-triazol-1-yl)-benzoic acid

생성물 1

HCID 21097217N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-(4-pyridin-3-yl-[1,2,3]triazol-1-yl)-benzamide

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

4-Methyl-3-(4-pyridin-3-yl-1,2,3-triazol-1-yl)-benzoic acid (76.3 mg; 0.272 mmol) was suspended in 5 mL of CH2Cl2, and 1 mL of THF, and 0.04 mL (0.4 mmol) of oxalyl chloride was added. One drop of DMF was then added to the stirring suspension, and the mixture was stirred for 2 h. The resulting cloudy solution was concentrated to dryness and suspended in CH2Cl2. N-(3-Amino-5-tert-butyl-2-methoxy-phenyl)-methane-sulfonamide (81 mg; 0.30 mmol) was added, then 0.06 mL (0.5 mmol) of 2,6-lutidine, and the resulting solution was stirred overnight. The mixture was then washed with 1M NaHSO4, saturated NaHCO3, and brine. The organic portion was dried with Na2SO4, filtered, and concentrated. Chromatography (0-6.5% MeOH in CH2Cl2), with careful selection of only the pure fractions, provided 80 mg (0.15 mmol; 55%) of Example 14. ESI MS m/z 535 [C27H30N6O4S+H]+.

후처리

  1. concentrationThe resulting cloudy solution was concentrated to dryness
  2. washThe mixture was then washed with 1M NaHSO4, saturated NaHCO3, and brine
  3. dry with materialThe organic portion was dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customChromatography (0-6.5% MeOH in CH2Cl2), with careful selection of only the pure fractions, provided 80 mg (0.15 mmol; 55%) of Example 14

출처 및 근거

ORD 기록
ord-fd0af20833874a808635d89f9ff130f5
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514458B2

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