Sodium Hydroxide → HCID 21913806, compound

HRID 1352626Notes

Reaction equation

HRID 1352626 reaction equation
C([O:3][C:4](=[O:34])[C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:14][CH2:15][CH2:16][N:17]2[C:25]3[C:24]([CH3:26])=[C:23]([CH3:27])[N:22]4[N:28]=[N:29][N:30]=[C:21]4[C:20]=3[N:19]=[C:18]2[CH2:31][CH2:32][CH3:33])(=[O:13])=[O:12])=[CH:7][CH:6]=1)C.[OH-].[Na+]>C(O)C>[CH3:27][C:23]1[N:22]2[N:28]=[N:29][N:30]=[C:21]2[C:20]2[N:19]=[C:18]([CH2:31][CH2:32][CH3:33])[N:17]([CH2:16][CH2:15][CH2:14][S:11]([C:8]3[CH:9]=[CH:10][C:5]([C:4]([OH:34])=[O:3])=[CH:6][CH:7]=3)(=[O:12])=[O:13])[C:25]=2[C:24]=1[CH3:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69412152HCID 69412152, compound

Product 1

HCID 21913806HCID 21913806, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-[3-(5,6-Dimethyl-8-propyl-7H-imidazo[4,5-c]tetrazolo[1,5-a]pyridin-7-yl)propane-1-sulfonyl]benzoic acid ethyl ester (2.50 g, 5.16 mmol), prepared as described in Parts A-E of Example 92 using the modification of Example 99, was treated with aqueous sodium hydroxide (10 mL of 1 N) in ethanol (26 mL), and the reaction stirred for two hours and became homogeneous. The solvents were removed under reduced pressure, and the residual white solid was dissolved in water (50 mL). The solution was washed with ethyl acetate (3×10 mL) and then adjusted to pH 4 with the addition of concentrated hydrochloric acid. A white solid precipitated, which was isolated by filtration, washed with water, and dried for three hours in a vacuum oven at 60° C. to provide 2.26 g of 4-[3-(5,6-dimethyl-8-propyl-7H-imidazo[4,5-c]tetrazolo[1,5-a]pyridin-7-yl)propane-1-sulfonyl]benzoic acid as a white solid.

Workup

  1. customThe solvents were removed under reduced pressure
  2. dissolutionthe residual white solid was dissolved in water (50 mL)
  3. washThe solution was washed with ethyl acetate (3×10 mL)
  4. additionadjusted to pH 4 with the addition of concentrated hydrochloric acid
  5. customA white solid precipitated
  6. customwhich was isolated by filtration
  7. washwashed with water
  8. customdried for three hours in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-61a299295a554d249c689a61a1cca7dd
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

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