Hydrochloric Acid → 2-[2-(Acetylamino)pyridin-4-yl]-4-(2-chlorophenyl)-1,3-thiazole-5-carboxylic acid

HRID 2282312Notes

Reaction equation

HRID 2282312 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[S:12][C:13]([C:23]([O:25]CC)=[O:24])=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[N:15]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].O.[OH-].[Li+].Cl>O1CCCC1.O>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[S:12][C:13]([C:23]([OH:25])=[O:24])=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[N:15]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 58095112Ethyl 2-[2-(acetylamino)pyridin-4-yl]-4-(2-chlorophenyl)-1,3-thiazole-5-carboxylate

Product 1

HCID 580949642-[2-(Acetylamino)pyridin-4-yl]-4-(2-chlorophenyl)-1,3-thiazole-5-carboxylic acidYield 100.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 2-[2-(acetylamino)pyridin-4-yl]-4-(2-chlorophenyl)-1,3-thiazole-5-carboxylate (0.249 g, 0.620 mmol) in tetrahydrofuran (1.670 mL) and water (0.100 mL) was added lithium hydroxide, monohydrate (0.037 g, 0.891 mmol) and stirred for 18 h. The mixture was acidified to pH 6 with aqueous 1N HCl (1.20 mL, 1.20 mmol) and extracted with EtOAc (10.0 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford the crude product (0.232 g) as a yellow solid and used without further purification. LC/MS (AA) ES+ 374, 376. 1H NMR (400 MHz, d6 DMSO) δ: 10.75 (br s, 1H), 8.69 (br s, 1H), 8.47-8.46 (m, 0.5H), 8.06-8.04 (m, 0.5H), 7.65-7.64 (m, 0.5H), 7.58-7.44 (m, 5H), 7.06-7.99 (m, 0.5H), 2.12 (s, 3H).

Workup

  1. extractionextracted with EtOAc (10.0 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a8abfd48cbfa4ac09f0533c9237071bc
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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