Tetrahydrofuran → 2-(4-(Benzo[d]thiazol-2-ylamino)phenoxy)nicotinic acid

HRID 410170Notes

Reaction equation

HRID 410170 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:27]=[CH:26][C:14]([O:15][C:16]2[N:25]=[CH:24][CH:23]=[CH:22][C:17]=2[C:18]([O:20]C)=[O:19])=[CH:13][CH:12]=1.C1COCC1.O.[OH-].[Li+]>O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:12]=[CH:13][C:14]([O:15][C:16]2[N:25]=[CH:24][CH:23]=[CH:22][C:17]=2[C:18]([OH:20])=[O:19])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 59326974HCID 59326974, compound

Product 1

HCID 462155562-(4-(Benzo[d]thiazol-2-ylamino)phenoxy)nicotinic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 2-(4-(benzo[d]thiazol-2-ylamino)phenoxy)nicotinate (0.70 g, 1.84 mmol) in a mixed solvent of THF (6 mL) and water (2 mL) was added lithium hydroxide monohydrate (0.39 mg, 9.2 mmol). The reaction mixture was stirred at RT for 16 h. The reaction was quenched with aqueous 2N HCl to pH 5. The precipitate formed was collected by filtration, washed with water, dried to provide 2-(4-(benzo[d]thiazol-2-ylamino)-phenoxy)nicotinic acid as off-white solid. MS (ESI, pos. ion) m/z: 364.0 (M+1). IC50 (uM) +.

Workup

  1. customThe reaction was quenched with aqueous 2N HCl to pH 5
  2. customThe precipitate formed
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-1620ab7bc4614862b88aaa3d1d4ab571
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

Loading…