Hydrazine → 3-(6-(6-(4-Fluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-2,2-dimethylpropanoic acid

HRID 1711796노트

반응식

HRID 1711796 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:17]=[N:18][C:19]([NH:22][NH2:23])=[CH:20][CH:21]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1.FC1C=CC(C2N=C3N(C=2)C=CO3)=CC=1.C1C(=O)N(I)C(=O)C1.FC1C=CC(B(O)O)=CN=1.NN.[CH3:59][C:60]1([CH3:67])[CH2:64][C:63](=O)[O:62][C:61]1=[O:66]>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:21]=[CH:20][C:19]4[N:18]([C:63]([CH2:64][C:60]([CH3:67])([CH3:59])[C:61]([OH:66])=[O:62])=[N:23][N:22]=4)[CH:17]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1

참가 물질

8

반응물 6

HCID 9321HydrazineHCID 870672,2-Dimethylsuccinic anhydrideHCID 120273N-IodosuccinimideHCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 574336106-(4-Fluorophenyl)-imidazo[2,1-b]oxazoleHCID 594577926-(4-Fluorophenyl)-5-(6-hydrazinylpyridin-3-yl)imidazo[2,1-b]oxazole

생성물 1

HCID 594578573-(6-(6-(4-Fluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-2,2-dimethylpropanoic acid수율 81%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

In a 100 mL round-bottom flask 6-(4-fluorophenyl)-5-(6-hydrazinylpyridin-3-yl)imidazo[2,1-b]oxazole (0.20 g, 0.65 mmol; prepared using A from 6-(4-fluorophenyl)-imidazo[2,1-b]oxazole [prepared according to WO2004110990A2, Example 1, Steps 1-3] with NIS, C using 2-fluoropyridine-5-boronic acid [Asymchem], D using hydrazine) and 3,3-dimethyldihydrofuran-2,5-dione (0.091 g, 0.71 mmol) were dissolved in 1,4-dioxane (5 mL) and the mixture was heated to about 100° C. After about 2 h the reaction was cooled to ambient temperature and concentrated in vacuo. The crude material was dissolved in DCM and crystallized upon the addition of Et2O. The resulting solid was filtered and dried under vacuum to provide the title compound as a white solid (0.22 g, 81%): LC/MS (Table 1, Method a) Rt, =1.86 min; MS m/z: 420.2 (M+H)+.

후처리

  1. customprepared
  2. temperatureAfter about 2 h the reaction was cooled to ambient temperature
  3. concentrationconcentrated in vacuo
  4. dissolutionThe crude material was dissolved in DCM
  5. customcrystallized upon the addition of Et2O
  6. filtrationThe resulting solid was filtered
  7. customdried under vacuum

출처 및 근거

ORD 기록
ord-2b1e1133338449c0904775669f4dbcda
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790741B2

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