HCID 67346507, 화합물 → N-(3-fluoro-4-(2-(4-oxocyclohex-1-enyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide

HRID 1676373노트

반응식

HRID 1676373 반응식
O1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[S:19][C:18]4[C:13](=[N:14][CH:15]=[CH:16][C:17]=4[O:20][C:21]4[CH:26]=[CH:25][C:24]([NH:27][C:28]([C:30]5[C:31](=[O:43])[N:32]([C:36]6[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=6)[N:33]=[CH:34][CH:35]=5)=[O:29])=[CH:23][C:22]=4[F:44])[CH:12]=3)=[CH:7][CH2:6]2)[O:4]CC1>C(O)(C(F)(F)F)=O>[F:44][C:22]1[CH:23]=[C:24]([NH:27][C:28]([C:30]2[C:31](=[O:43])[N:32]([C:36]3[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=3)[N:33]=[CH:34][CH:35]=2)=[O:29])[CH:25]=[CH:26][C:21]=1[O:20][C:17]1[CH:16]=[CH:15][N:14]=[C:13]2[CH:12]=[C:11]([C:8]3[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH:7]=3)[S:19][C:18]=12

참가 물질

3

반응물 1

HCID 67346507HCID 67346507, 화합물

생성물 1

HCID 58949478N-(3-fluoro-4-(2-(4-oxocyclohex-1-enyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide수율 28.7%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

A round-bottomed flask was charged with N-(4-(2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide (153 mg, 0.249-mmol) and CF3COOH (10 mL). The reaction mixture was stirred at room temperature until the starting material had been consumed (overnight). Then the solvent was removed and the residue was purified by silica gel chromatography (dichloromethane/7 M NH3 in MeOH from 50/1 to 10/1, v/v) to give product (40.8 mg, 28.7%). LRMS (APCI pos): >99% purity, 254 nm, m/e 571 (M+1). 1H NMR (400 MHz, CDCl3) δ 11.84 (s, 1H), 8.45 (d, 1H), 8.41 (d, 1H), 8.24 (d, 1H), 7.96 (d, 1H), 7.58-7.62 (m, 2H), 7.40 (m, 1H), 7.20-7.28 (m, 4H), 6.51 (d, 1H), 6.42 (m, 1H), 3.14 (m, 2H), 3.02 (m, 2H), 2.71 (m, 2H).

후처리

  1. customhad been consumed (overnight)
  2. customThen the solvent was removed
  3. customthe residue was purified by silica gel chromatography (dichloromethane/7 M NH3 in MeOH from 50/1 to 10/1

출처 및 근거

ORD 기록
ord-15a59ef1424d4693b106837adf88d60c
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003662B2

반응 노트

불러오는 중…