HCID 86702340, compound → HCID 86702339, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[C:14]3=[N:15][C:16]([NH:19][C@H:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=4)[CH3:21])=[CH:17][CH:18]=[C:13]3[N:12]=[CH:11]2)[C:5]([O:8]C)=[N:6][CH:7]=1>Br>[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[C:14]3=[N:15][C:16]([NH:19][C@H:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=4)[CH3:21])=[CH:17][CH:18]=[C:13]3[N:12]=[CH:11]2)[C:5](=[O:8])[NH:6][CH:7]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A suspension of 3-(5-chloro-2-methoxypyridin-3-yl)-N-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-3H-imidazo[4,5-b]pyridin-5-amine (Preparation 24d, 69 mg, 0.17 mmol) in aqueous hydrogen bromide solution (48%, 0.6 mL) was heated to 100° C. for 3 hours. After cooling to ambient temperature, water was removed under reduced pressure and the residue was treated with acetonitrile. The solid was filtered, washed with acetonitrile and dried to give the title compound as a hydrobromide salt (80 mg). The solid was then added to a stirred solution of aqueous saturated potassium carbonate (10 mL) and the resulting suspension was stirred for 2 hours. Ethyl acetate (15 mL) was added and the aqueous layer was separated and washed with ethyl acetate (2×15 mL). The combined organic extracts were dried over sodium sulphate and the solvents evaporated in vacuo to yield the title compound (44 mg, 66%) as a pink solid.
Workup
- temperatureAfter cooling to ambient temperature
- customwater was removed under reduced pressure
- additionthe residue was treated with acetonitrile
- filtrationThe solid was filtered
- washwashed with acetonitrile
- customdried
Sources & evidence
- ORD record
- ord-3adf3bafb4d94a8f9e982e22f63b36b8
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133200B2
Reaction notes
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