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

HRID 1880037Notes

Reaction equation

HRID 1880037 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-77ce4aef1c3143e2bcf7fb5bade8d05c
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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