Hydrochloric Acid → 3-(2-Fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid (2-hydroxy-ethoxy)-amide

HRID 1366798Notes

Reaction equation

HRID 1366798 reaction equation
C([O:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[S:18][C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[C:11]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([S:26][CH3:27])=[CH:22][C:21]=1[F:28])=[O:9])=C.Cl>CO>[OH:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[S:18][C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[C:11]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([S:26][CH3:27])=[CH:22][C:21]=1[F:28])=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 597038883-(2-Fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid (2-vinyloxy-ethoxy)-amide

Product 1

HCID 250297823-(2-Fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid (2-hydroxy-ethoxy)-amideYield 47.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(2-Fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid (2-vinyloxy-ethoxy)-amide (20 mg, 0.048 mmol) was dissolved in methanol (1 ml) and treated with concentrated hydrochloric acid (0.01 ml, 0.12 mmol) before being stirred at room temperature for 2 hours. The reaction mixture was concentrated in vacuo and the resultant residue subjected to reverse phase HPLC (0.1% HCO2H in water on a gradient of acetonitrile). The appropriate fractions were combined and freeze-dried to give the title compound (9 mg, 47%). LCMS (method A): RT=6.36 min, M+H+ 394; 1H NMR (DMSO-d6, 400 MHz) 3.58 (2H, t, J=4.89 Hz), 3.84 (2H, t, J=4.91 Hz), 6.89 (1H, t, J=8.76 Hz), 6.98 (1H, dd, J=8.41, 2.15 Hz), 7.21-7.26 (1H, m), 8.02 (1H, d, J=5.61 Hz), 8.45 (1H, dd, J=8.25, 5.61 Hz), 8.53-8.59 (1H, m).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customfreeze-dried

Sources & evidence

ORD record
ord-77bbbacfe27e4b318d3ee3670f8d4260
Source dataset
uspto-grants-2011_02
Patent number
US07893085B2

Reaction notes

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