Dimethylamine, hydrochloride → Ethyl 4-[4-(difluoromethyl)phenoxy]-2-[(dimethylamino)-carbonyl]-1-benzofuran-6-carboxylate

HRID 1177294노트

반응식

HRID 1177294 반응식
[F:1][CH:2]([F:27])[C:3]1[CH:26]=[CH:25][C:6]([O:7][C:8]2[C:13]3[CH:14]=[C:15]([C:17](O)=[O:18])[O:16][C:12]=3[CH:11]=[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:9]=2)=[CH:5][CH:4]=1.[CH3:28][N:29](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:30].F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.CNC>CN(C=O)C.O>[F:1][CH:2]([F:27])[C:3]1[CH:26]=[CH:25][C:6]([O:7][C:8]2[C:13]3[CH:14]=[C:15]([C:17]([N:29]([CH3:30])[CH3:28])=[O:18])[O:16][C:12]=3[CH:11]=[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:9]=2)=[CH:5][CH:4]=1

참가 물질

7

반응물 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 595601994-[4-(Difluoromethyl)phenoxy]-6-(ethoxycarbonyl)-1-benzofuran-2-carboxylic acid

생성물 1

HCID 59560302Ethyl 4-[4-(difluoromethyl)phenoxy]-2-[(dimethylamino)-carbonyl]-1-benzofuran-6-carboxylate수율 74.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To a solution of 4-[4-(difluoromethyl)phenoxy]-6-(ethoxycarbonyl)-1-benzofuran-2-carboxylic acid (300 mg, 0.80 mmol) in DMF (10 mL) was added HATU (606 mg, 1.59 mmol), DIEA (515 mg, 4.0 mmol) and the solution was stirred at 0° C. for 15 min. Dimethylamine hydrochloride (97.5 mg, 1.20 mmol) was added and the solution was warmed gradually to room temperature and stirred for 14 h. Water was added to the reaction and the product was extracted with CHCl3. The combined organic layers were washed with water twice, dried over MgSO4, and concentrated. The product was purified via gradient silica gel chromatography using CHCl3/MeOH (100/0 to 95/5) to give the title compound (240 mg, 70%) as a light yellow solid. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.38 (t, J=7.16 Hz, 3 H) 3.13 (s, 3 H) 3.32 (s, 3 H) 4.38 (q, J=7.16 Hz, 2 H) 6.64 (t, J=56.61 Hz, 1 H) 7.09 (d, J=8.48 Hz, 2 H) 7.16 (s, 1 H) 7.50 (d, J=8.48 Hz, 2 H) 7.55 (s, 1 H) 8.05 (s, 1 H).

후처리

  1. temperaturethe solution was warmed gradually to room temperature
  2. stirringstirred for 14 h
  3. extractionthe product was extracted with CHCl3
  4. washThe combined organic layers were washed with water twice
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe product was purified via gradient silica gel chromatography

출처 및 근거

ORD 기록
ord-53fcd05ac7624cffb5977de6e25088f8
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842713B2

반응 노트

불러오는 중…