8-(4-Cyclopropyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid (2-vinyloxy-ethoxy)-amide → 8-[(4-Cyclopropyl-2-Fluorophenyl)amino]-N-(2-Hydroxyethoxy)imidazo[1,5-A]pyridine-7-Carboxamide
Reaction equation
C([O:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[CH:15]=[CH:14][N:13]2[CH:16]=[N:17][CH:18]=[C:12]2[C:11]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]2[CH2:28][CH2:27]2)=[CH:22][C:21]=1[F:29])=[O:9])=C>CO.ClCCl>[OH:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[CH:15]=[CH:14][N:13]2[CH:16]=[N:17][CH:18]=[C:12]2[C:11]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]2[CH2:28][CH2:27]2)=[CH:22][C:21]=1[F:29])=[O:9]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
8-(4-Cyclopropyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid (2-vinyloxy-ethoxy)-amide (56 mg, 0.14 mmol) was dissolved in methanol and loaded onto an Isolute® SCX-2 cartridge (5 g). The cartridge was then washed with methanol and the desired product was subsequently eluted using 2M NH3 in MeOH. The eluent was collected and concentrated to give a residue. The residue was subjected to flash chromatography (Si-PPC, gradient 0% to 20%, methanol in dichloromethane) to afford the title compound as a pale yellow solid (37 mg, 71%). LCMS (method A): RT=6.40 min, [M+H]+=371. 1H NMR (CH3OH-d4): 8.20 (1 H, d, J=0.71 Hz), 7.67-7.65 (1 H, m), 7.17-7.11 (1 H, m), 6.94-6.87 (2H, m), 6.73 (1 H, d, J=7.38 Hz), 6.39 (1 H, s), 4.00-3.97 (2 H, m), 3.75-3.72 (2 H, m), 1.98-1.89 (1 H, m), 1.04-0.98 (2 H, m), 0.73-0.68 (2 H, m).
Workup
- washThe cartridge was then washed with methanol
- washthe desired product was subsequently eluted
- customThe eluent was collected
- concentrationconcentrated
- customto give a residue
Sources & evidence
- ORD record
- ord-8407ec5a85f142d586631f6aa4a98bc2
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293763B2
Reaction notes
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