Hydrochloric Acid → 2-(7-Chlorothieno[3,2-b]pyridin-2-yl)-1,3-thiazole-4-carboxylic acid

HRID 1825115Notes

Reaction equation

HRID 1825115 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[S:12][CH:13]=[C:14]([C:16]([O:18]C)=[O:17])[N:15]=3)[S:10][C:3]=12.[OH-].[Na+].Cl>CCOC(C)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[S:12][CH:13]=[C:14]([C:16]([OH:18])=[O:17])[N:15]=3)[S:10][C:3]=12

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22143578Methyl 2-(7-chlorothieno[3,2-b]pyridin-2-yl)-1,3-thiazole-4-carboxylate

Product 1

HCID 221435862-(7-Chlorothieno[3,2-b]pyridin-2-yl)-1,3-thiazole-4-carboxylic acidYield 98.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 2-(7-chlorothieno[3,2-b]pyridin-2-yl)-1,3-thiazole-4-carboxylate (0.200 g, 0.62 mmole), prepared by the method described in PC10795A, section A, example 26, in EtOAc (5 ml) was added 1N aqueous NaOH solution (1.85 ml, 1.85 mmole). The reaction mixture was stirred at 50° C. for 1 h, cooled to room temperature, diluted with H2O (10 ml) and acidified with 1N HCl to pH˜2. The resulting solution was extracted with 10% MeOH in CH2Cl2 (5×10 ml), dried over MgSO4 and concentrated and dried under vacuum to give yellow solid (0.181 g, 98%). 1H NMR (300 MHz, DMSO-d6) □ 7.67 (1H, d, J=5.09 Hz) 8.41 (1H, s) 8.65 (1H, s) 8.71 (1H, bs); ESIMS (MH+): 309.95.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe resulting solution was extracted with 10% MeOH in CH2Cl2 (5×10 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customdried under vacuum

Sources & evidence

ORD record
ord-5c858ff59d8740c281c006b5c0b8c837
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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