Sodium Hydroxide → 2-Tert-butoxy-2-[2-methyl-4-(1-methylpyrazol-4-yl)-5,6,7,8-tetrahydrobenzothiopheno[2,3-b]pyridin-3-yl]acetic acid

HRID 1627903Notes

Reaction equation

HRID 1627903 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:5]2=[C:4]([C:15]2[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=2)[C:3]=1[CH:21]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:22]([O:24]C)=[O:23].[OH-].[Na+]>CO>[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:5]2=[C:4]([C:15]2[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=2)[C:3]=1[CH:21]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:22]([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 49804990Methyl 2-[2-methyl-4-(1-methyl-1H-pyrazol-4-yl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]-2-tert-butoxyacetate

Product 1

HCID 498048592-Tert-butoxy-2-[2-methyl-4-(1-methylpyrazol-4-yl)-5,6,7,8-tetrahydrobenzothiopheno[2,3-b]pyridin-3-yl]acetic acidYield 29.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 2-[2-methyl-4-(1-methyl-1H-pyrazol-4-yl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]-2-tert-butoxyacetate (0.120 g; 0.281 mmol) in methanol (3.5 mL) was added a solution of sodium hydroxide 10 N (0.350 mL; 3.5 mmol) and the mixture was heated at 60° C. for 18 h. The volatiles were removed under reduced pressure and the residue was dissolved in water, the mixture was then acidified by adding 1N HCl until a precipitate was formed. The solid was filtered, washed with water and dried under reduced pressure. The crude product was suspended in a mixture of acetonitrile and methanol, filtered, washed with acetonitrile and dried under reduced pressure to furnish 0.034 g (29%) of the title compound as a white solid.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. additionby adding 1N HCl until a precipitate
  4. customwas formed
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customdried under reduced pressure
  8. additionThe crude product was suspended in a mixture of acetonitrile and methanol
  9. filtrationfiltered
  10. washwashed with acetonitrile
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-c1424bce0fa04556854bd56486cb92f8
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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