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 1711796Notes

Reaction equation

HRID 1711796 reaction equation
[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

Participants

8

Reactant 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

Product 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 acidYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-2b1e1133338449c0904775669f4dbcda
Source dataset
uspto-grants-2010_09
Patent number
US07790741B2

Reaction notes

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