p-Anisoyl chloride → N-(3-(isothiazolo[5,4-b]pyridin-3-ylamino)propyl)-4-methoxybenzamide

HRID 502591노트

반응식

HRID 502591 반응식
[S:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([NH:10][CH2:11][CH2:12][CH2:13][NH2:14])=[N:2]1.C(N(C(C)C)CC)(C)C.[CH3:24][O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1>C(Cl)Cl>[S:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([NH:10][CH2:11][CH2:12][CH2:13][NH:14][C:30](=[O:31])[C:29]2[CH:33]=[CH:34][C:26]([O:25][CH3:24])=[CH:27][CH:28]=2)=[N:2]1

참가 물질

5

반응물 3

HCID 7477p-Anisoyl chlorideHCID 81531DiisopropylethylamineHCID 58727204N1-(isothiazolo[5,4-b]pyridin-3-yl)propane-1,3-diamine

생성물 1

HCID 57436521N-(3-(isothiazolo[5,4-b]pyridin-3-ylamino)propyl)-4-methoxybenzamide수율 32.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

N1-(Isothiazolo[5,4-b]pyridin-3-yl)propane-1,3-diamine (100 mg, 0.48 mmol) was dissolved in anhydrous methylene chloride with diisopropylethylamine (0.23 mL, 1.34 mmol). The mixture was cooled in an ice-bath under nitrogen and a solution of 4-methoxybenzoyl chloride (98 mg, 0.58 mmol) in methylene chloride (5 mL) was added drop-wise. After the addition was completed the ice-bath was removed and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with methylene chloride and then washed successively with saturated sodium bicarbonate solution and brine. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by prep-scale reverse phase high performance liquid chromatography to yield N-(3-(isothiazolo[5,4-b]pyridin-3-ylamino)propyl)-4-methoxybenzamide (54 mg). 1H NMR (300 MHz, DMSO-d6): 8.68 (d, 1H), 8.55 (t, 1H), 8.45 (d, 1H), 8.18 (s, 1H), 7.82-7.85 (m, 2H), 7.41 (dd, 1H), 7.26-7.36 (m, 2H), 3.95 (s, 3H), 3.40-3.42 (dd, 2H), 3.39-3.40 (dd, 2H), 1.82-1.95 ppm (m, 2H). MW=342 confirmed by LC-MS, tr=10.82 min (Method Y) MH+=343.

후처리

  1. temperatureThe mixture was cooled in an ice-bath under nitrogen
  2. additionAfter the addition
  3. customwas removed
  4. additionThe reaction mixture was diluted with methylene chloride
  5. washwashed successively with saturated sodium bicarbonate solution and brine
  6. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by prep-scale reverse phase high performance liquid chromatography

출처 및 근거

ORD 기록
ord-430ec040fa144f82aaf4718c7cc672a4
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776847B2

반응 노트

불러오는 중…