Dimethylformamide → 1-(8-Fluoro-2-phenyl-quinolin-7-yl)-3-([1,3,4]thiadiazol-2-ylsulfanyl)-imidazo[1,5-a]pyrazin-8-ylamine
Reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8](=[S:28])[NH:9][C:10]=2[C:11]2[C:20]([F:21])=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.Br[C:30]1[S:31][CH:32]=[N:33][N:34]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>>[F:21][C:20]1[C:11]([C:10]2[N:9]=[C:8]([S:28][C:30]3[S:31][CH:32]=[N:33][N:34]=3)[N:4]3[CH:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=23)=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[C:17]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:16]=[CH:15]2Participants
Reactant 4
Product 1
Conditions
- Temperature
- 100 °C
Procedure
A 10 mL microwave vessel was charged with a solution of 8-amino-1-(8-fluoro-2-phenyl-quinolin-7-yl)-2H-imidazo[1,5-a]pyrazine-3-thione (20 mg, 0.00005 mol), 2-bromo-1,3,4-thiadiazole (0.017 g, 0.00010 mol) and potassium carbonate (0.021 g, 0.00015 mol) in DMF (1.4 mL, 0.018 mol). The reaction mixture was heated in the microwave at 100° C. for 10 min. The reaction mixture was concentrated in vacuo and purification by Gilson HPLC eluting with 10→65% acetonitrile: H2O afforded the title compound as a light yellow solid. 1H NMR (400 MHz, CDCl3): δ=7.31 (d, J=5.05 Hz, 1H), 7.47-7.58 (m, 3H), 7.69-7.80 (m, 3H), 8.05 (d, J=8.84 Hz, 1H), 8.24 (dd, J=8.34, 1.52 Hz, 2H), 8.32 (dd, J=8.72, 1.39 Hz, 1H), 9.07 (s, 1H). MS(ES+): m/z 472.13 (100)[MH+]. HPLC: tR=2.9 min (Open Lynx polar—5 min).
Workup
- concentrationThe reaction mixture was concentrated in vacuo and purification by Gilson HPLC
- washeluting with 10→65% acetonitrile
Sources & evidence
- ORD record
- ord-0cffeb3867f94acd93136b95c11b0233
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07648987B2
Reaction notes
Loading…