Water → HCID 24966199, 화합물

HRID 1666519노트

반응식

HRID 1666519 반응식
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=[C:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH:17]=2)=[N:13][CH:14]=1.[N:29]1[CH:34]=[CH:33][CH:32]=[C:31]([NH:35][C:36](=O)[O:37]C2C=CC=CC=2)[N:30]=1.C(N(CC)CC)C.O>CS(C)=O>[F:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=2)[CH:22]=[C:23]2[CH2:24][CH2:25][N:26]([C:36]([NH:35][C:31]3[N:30]=[N:29][CH:34]=[CH:33][CH:32]=3)=[O:37])[CH2:27][CH2:28]2)=[N:13][CH:14]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 20150036Phenyl pyridazin-3-ylcarbamateHCID 66876197HCID 66876197, 화합물

생성물 1

HCID 24966199HCID 24966199, 화합물수율 42%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A solution of 5-fluoro-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine trifluoroacetate (0.466 g), phenyl pyridazin-3-ylcarbamate (0.274 g, 1.40 equiv), and triethylamine (0.634 mL, 5.00 equiv) in dimethyl sulfoxide (2.0 mL, 0.30 M) was heated to 65° C. for 2 h. The reaction was cooled to room temperature. Water was added and then the solution was extracted with ethyl acetate (3 times). The organic extracts were combined and washed with water, dried over magnesium sulfate, filtered, and concentrated. The residue was purified on a 12 g silica gel column using 20-50% ethyl acetate/dichloromethane over 60 minutes as the eluent to give the title compound as a yellow foam. 0.155 g, 42% yield. 1H NMR (400 MHz, CDCl3) δ ppm 2.46 (2H, t, J=5.5 Hz), 2.59 (2H, t, J=5.5 Hz), 3.61 (2H, t, J=5.8 Hz), 3.71 (2H, t, J=5.8 Hz), 6.39 (1H, s), 6.84-6.99 (3H, m), 7.02 (1H, d, J=7.8 Hz), 7.34 (1H, t, J=7.8 Hz), 7.39-7.54 (2H, m), 8.02 (1H, d, J=3.1 Hz), 8.47 (1H, d, J=8.6 Hz), 8.74 (1H, d, J=3.5 Hz).

후처리

  1. extractionthe solution was extracted with ethyl acetate (3 times)
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on a 12 g silica gel column
  7. customover 60 minutes

출처 및 근거

ORD 기록
ord-2593945ce2dd4ade9f6e24981cac461b
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044052B2

반응 노트

불러오는 중…