Water → 4-(4-chlorophenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide

HRID 1977412Notes

Reaction equation

HRID 1977412 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:12]=[N:11][CH:10]=[C:9]3[S:13][C:14]([C:16](OC)=[O:17])=[CH:15][C:8]=23)=[CH:4][CH:3]=1.[CH3:22][NH2:23].[H-].[Na+].O>C1COCC1>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:12]=[N:11][CH:10]=[C:9]3[S:13][C:14]([C:16]([NH:23][CH3:22])=[O:17])=[CH:15][C:8]=23)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 24758Sodium hydrideHCID 10892544Methyl 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylate

Product 1

HCID 98835044-(4-chlorophenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 61A (100 mg, 0.3135 mmol) and methylamine (2M solution in THF, 0.467 mL, 0.941 mmol) in THF (2 mL) at 0° C. was treated with NaH (12 mg, 0.47 mmol), stirred at room temperature for 1 hour, treated with water (0.1 mL), and concentrated. The residue was purified by flash chromatography on silica gel with 20% acetone/hexane to provide the title compound.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography on silica gel with 20% acetone/hexane

Sources & evidence

ORD record
ord-b88142d0120348c58856f3009b114209
Source dataset
uspto-grants-2001_05
Patent number
US06232320B1

Reaction notes

Loading…