Lithium hydroxide, monohydrate → HCID 24826505, compound

Reaction equation

[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:18]=[C:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22][CH:21]=3)[C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][N:9]=2)[S:5][CH:6]=1.O.[OH-].[Li+]>C1COCC1.O>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:18]=[C:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22][CH:21]=3)[C:11]([C:12]([OH:14])=[O:13])=[CH:10][N:9]=2)[S:5][CH:6]=1

Participants

Procedure

Ethyl 6-(4-methylthiazol-2-ylamino)-4-(naphthalen-1-yloxy)nicotinate (1.00 g, 2.47 mmol) was dissolved in THF (5 mL). A solution of lithium hydroxide hydrate (0.207 g, 4.93 mmol) in water (1 mL) was added, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated, 2M HCl was added to adjust the pH to 3. The reaction mixture was filtered to obtain the desired product (0.61 g, 65.5% yield) as a white solid. 1H NMR (d6-DMSO) δ 10.85 (bs, 1H), 8.76 (s, 1H), 8.06 (d, 1H), 7.88-7.93 (m, 2H), 7.55-7.65 (m, 3H), 7.35 (d, 1H), 6.58 (s, 1H), 6.32 (s, 1H), 2.14 (s, 3H).