Potassium trimethylsilanolate → (3-Amino-5-chloro-2-cyclopropylcarbamoyl-4-methyl-thieno[2,3-b]pyridin-6-yloxy)-acetic acid

HRID 656645Notes

Reaction equation

HRID 656645 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][O:5][C:6]1[N:11]=[C:10]2[S:12][C:13]([C:16](=[O:21])[NH:17][CH:18]3[CH2:20][CH2:19]3)=[C:14]([NH2:15])[C:9]2=[C:8]([CH3:22])[C:7]=1[Cl:23].C[Si](C)(C)[O-].[K+]>C1COCC1>[NH2:15][C:14]1[C:9]2[C:10](=[N:11][C:6]([O:5][CH2:4][C:3]([OH:24])=[O:2])=[C:7]([Cl:23])[C:8]=2[CH3:22])[S:12][C:13]=1[C:16](=[O:21])[NH:17][CH:18]1[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 68436041(3-Amino-5-chloro-2-cyclopropylcarbamoyl-4-methyl-thieno[2,3-b]pyridin-6-yloxy)-acetic acid methylester

Product 1

HCID 68436813(3-Amino-5-chloro-2-cyclopropylcarbamoyl-4-methyl-thieno[2,3-b]pyridin-6-yloxy)-acetic acidYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-amino-5-chloro-2-cyclopropylcarbamoyl-4-methyl-thieno[2,3-b]pyridin-6-yloxy)-acetic acid methyl ester (0.940 g, 2.54 mmol) in THF (20 ml) is added 95% potassium trimethylsilanolate (1.63 g, 12.71 mmol). The resulting mixture is stirred at room temperature for 2 hours and then quenched by the addition of water (50 ml). The mixture is acidified to pH2 by the addition of 1 N HCl, and then extracted with EtOAc (100 ml). The organic layer is washed with brine (40 ml), then dried (anhydrous magnesium sulfate), filtered, and concentrated to give the title compound as a yellow solid (0.693 g, 77%). Mass (m/z): 355.9 (M++1), 354.0 (M+−1).

Workup

  1. customquenched by the addition of water (50 ml)
  2. additionThe mixture is acidified to pH2 by the addition of 1 N HCl
  3. extractionextracted with EtOAc (100 ml)
  4. washThe organic layer is washed with brine (40 ml)
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-666775453ac94cc7bc4cc9b21619dacf
Source dataset
uspto-grants-2011_12
Patent number
US08071776B2

Reaction notes

Loading…