Lithium hydroxide, monohydrate → HCID 24826505, compound

HRID 910971Notes

Reaction equation

HRID 910971 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

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 24825976HCID 24825976, compound

Product 1

HCID 24826505HCID 24826505, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

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).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition2M HCl was added
  3. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-1bd7fd5fba2f4b3ba09d41526eae20f1
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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