Sodium Acetate → 1,2-Diethyl 4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]tetrahydro-1,2-pyridazinedicarboxylate

HRID 75172노트

반응식

HRID 75172 반응식
[NH2:1][C:2](=[S:19])[CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:4]1.Br[CH2:21][C:22]([C:24]1[CH2:28][CH:27]([C:29]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:30]=2[F:36])[O:26][N:25]=1)=O.C([O-])(=O)C.[Na+]>CO>[F:36][C:30]1[CH:31]=[CH:32][CH:33]=[C:34]([F:35])[C:29]=1[CH:27]1[O:26][N:25]=[C:24]([C:22]2[N:1]=[C:2]([CH:3]3[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:4]3)[S:19][CH:21]=2)[CH2:28]1

참가 물질

5

반응물 3

HCID 517045Sodium AcetateHCID 866575632-Bromo-1-(4,5-dihydro-5-(2,6-difluorophenyl)-3-isoxazolyl)ethanone2회HCID 866744641,2-Diethyl 4-(aminothioxomethyl)tetrahydro-1,2-pyridazinedicarboxylate2회

생성물 1

HCID 866744651,2-Diethyl 4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]tetrahydro-1,2-pyridazinedicarboxylate

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
35 °C

실험 절차

A mixture of 1,2-diethyl 4-(aminothioxomethyl)tetrahydro-1,2-pyridazinedicarboxylate (i.e. the product of Step F) (2.58 g, 0.0089 mol) and 2-bromo-1-(4,5-dihydro-5-(2,6-difluorophenyl)-3-isoxazolyl)ethanone (i.e the product of Step C) (2.63 g, 0.0086 mol) in methanol (20 mL) were carefully heated to 35° C. No exotherm was observed and the temperature was raised to between 45 to 50° C. and held at this temperature for 1 h. The reaction mixture was neutralised with aqueous sodium acetate (0.73 g in about 20 mL water). The reaction mixture was extracted with diethyl ether (3×), dried magnesium sulfate, filtered, and concentrated under reduced pressure to provide the title compound (4.18 g), which was used without purification.

후처리

  1. temperaturethe temperature was raised to between 45 to 50° C.
  2. extractionThe reaction mixture was extracted with diethyl ether (3×), dried magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ff949c2df7874969a9d53c14b01d5ec4
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835427B2

반응 노트

불러오는 중…