Sodium Hydroxide → 2-(3-(Benzyloxy)-5-bromopyridin-2-ylamino)thiazolo[5,4-b]pyridine-6-carboxylic acid
Reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]2[S:18][C:19]3[C:24]([N:25]=2)=[CH:23][C:22]([C:26]([O:28]C)=[O:27])=[CH:21][N:20]=3)=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CCO>[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]2[S:18][C:19]3[C:24]([N:25]=2)=[CH:23][C:22]([C:26]([OH:28])=[O:27])=[CH:21][N:20]=3)=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 10 mL round-bottomed flask was charged with methyl 2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazolo[5,4-b]pyridine-6-carboxylate (80 mg, 0.17 mmol) and EtOH (3 mL). Sodium hydroxide (0.51 ml, 0.51 mmol) was added and stirred overnight. The methanol was removed and the residue was partitioned between methylene chloride and 0.5 N HCl. Solid K2CO3 was added to adjust to pH 5 and additional methanol was added. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo to afford the title compound (80 mg, 103% yield) as an off-white solid. 1H NMR (DMSO-d6) δ 11.0 (bs, 1H), 8.85 (d, 1H), 8.26 (d, 1H), 8.10 (d, 1H), 7.75 (d, 1H), 7.61 (d, 2H), 7.42 (t, 2H), 7.36 (m, 1H), 5.33 (s, 2H). Mass spectrum (apci) m/z=457.1 (M+H).