Hydrochloric Acid → 4-{2-[5-(2-Chloro-phenyl)-pyridin-2-yloxy]-acetylamino}-thiophene-3-carboxylic acid

HRID 14606Notes

Reaction equation

HRID 14606 reaction equation
C[O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:27])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])=[CH:16][N:15]=2)=[CH:8][S:7][CH:6]=1)=[O:4].[OH-].[Na+].C1COCC1.Cl>C(O)C.O>[Cl:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:17]1[CH:18]=[CH:19][C:14]([O:13][CH2:12][C:11]([NH:10][C:9]2[C:5]([C:3]([OH:4])=[O:2])=[CH:6][S:7][CH:8]=2)=[O:27])=[N:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 686913934-{2-[5-(2-Chloro-phenyl)-pyridin-2-yloxy]-acetylamino}-thiophene-3-carboxylic acid methyl ester

Product 1

HCID 160681584-{2-[5-(2-Chloro-phenyl)-pyridin-2-yloxy]-acetylamino}-thiophene-3-carboxylic acidYield 67%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 4-{2-[5-(2-chloro-phenyl)-pyridin-2-yloxy]-acetylamino}-thiophene-3-carboxylic acid methyl ester (79 mg) in ethanol (10 mL) was added a solution of sodium hydroxide (1M, 0.392 mL) and THF (8 mL) and the reaction mixture was stirred at room temperature over night. After such time the reaction mixture was acidified by addition of a solution of hydrochloric acid (1N, 0.395 mL) and then water was added. The precipitate was isolated by filtration, washed with water and dried in vacuo to yield 4-{2-[5-(2-chloro-phenyl)-pyridin-2-yloxy]-acetylamino}-thiophene-3-carboxylic acid (51 mg, 67%).

Workup

  1. customThe precipitate was isolated by filtration
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-1fcd2dc531ed4a749a1a5f027192250b
Source dataset
uspto-grants-2010_06
Patent number
US07732452B2

Reaction notes

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