Sodium Hydroxide → 3-(2-Fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid

HRID 1366796Notes

Reaction equation

HRID 1366796 reaction equation
C([O:3][C:4]([C:6]1[S:14][C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][C:17]=1[F:24])=[O:5])C.[OH-].[Na+]>>[F:24][C:17]1[CH:18]=[C:19]([S:22][CH3:23])[CH:20]=[CH:21][C:16]=1[NH:15][C:7]1[C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[S:14][C:6]=1[C:4]([OH:5])=[O:3]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 597038903-(2-Fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 597039013-(2-Fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acidYield 61.5%

Conditions

Temperature
60 °C

Procedure

A suspension of 3-(2-fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester (0.19 g, 0.52 mmol) in IMS (10 ml) was treated with sodium hydroxide (1M aqueous solution, 0.63 ml) and the reaction mixture heated at 60° C. for 3 hours. The resultant mixture was allowed to cool then concentrated in vacuo. The crude residue was treated with water and the mixture adjusted to pH 5 with acetic acid. The resultant suspension was filtered, the residue collected and dried in vacuo to give the title compound as a green solid (0.107 g, 56%) which was used without purification in the subsequent step.

Workup

  1. temperatureto cool
  2. concentrationthen concentrated in vacuo
  3. additionThe crude residue was treated with water
  4. filtrationThe resultant suspension was filtered
  5. customthe residue collected
  6. customdried in vacuo

Sources & evidence

ORD record
ord-c2664d17976643b6b3f0f9bfe6d0cd39
Source dataset
uspto-grants-2011_02
Patent number
US07893085B2

Reaction notes

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