Triethylamine → Methyl 2-{[(5-methylpyridin-3-yl)amino]sulfonyl}benzoate

HRID 252208

반응식

HRID 252208 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.C(N(CC)CC)C.Cl[S:17]([C:20]1[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23])(=[O:19])=[O:18]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][S:17]([C:20]2[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=2[C:22]([O:24][CH3:25])=[O:23])(=[O:19])=[O:18])[CH:5]=[N:6][CH:7]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl esterHCID 27628943-Amino-5-methylpyridine

생성물 1

HCID 58924073Methyl 2-{[(5-methylpyridin-3-yl)amino]sulfonyl}benzoate수율 34%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of 5-methylpyridin-3-amine (0.5 g, 4.62 mmol) in CH2Cl2 (50 ml) were added triethylamine (0.64 mL, 4.62 mmol) and methyl 2-(chlorosulfonyl)benzoate (1.08 g, 4.62 mmol). The resulting mixture was stirred at room temperature for 1 hour. The mixture was then diluted with saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash chromatography (0-8% MeOH/CH2Cl2) to give the title compound (0.476 g, 34%). 1H NMR (400 MHz, DMSO-D6) δ ppm 10.25-10.62 (m, 1H) 8.6 (s, 2H) 7.81-7.93 (m, 1H) 7.64-7.76 (m, 2H) 7.54-7.64 (m, 1H) 7.28 (s, 1H) 3.80 (s, 3H) 2.18 (s, 3H).

후처리

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash chromatography (0-8% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-6f001939915e4bf99a8728db4c5e78d8
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868026B2

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