Hydrochloric Acid → 4-(4-{[(3-Cyano-4-phenyl-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl)sulfanyl]methyl}-1,3-thiazol-2-yl)benzoic acid

HRID 1916275Notes

Reaction equation

HRID 1916275 reaction equation
[C:1]([C:3]1[C:4]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:5]2[CH2:28][CH2:27][CH2:26][C:6]2=[N:7][C:8]=1[S:9][CH2:10][C:11]1[N:12]=[C:13]([C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=2)[S:14][CH:15]=1)#[N:2].[OH-].[Na+].Cl>O1CCOCC1>[C:1]([C:3]1[C:4]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:5]2[CH2:28][CH2:27][CH2:26][C:6]2=[N:7][C:8]=1[S:9][CH2:10][C:11]1[N:12]=[C:13]([C:16]2[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)[S:14][CH:15]=1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 44133054Methyl 4-(4-{[(3-cyano-4-phenyl-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl)sulfanyl]methyl}-1,3-thiazol-2-yl)benzoate

Product 1

HCID 441328904-(4-{[(3-Cyano-4-phenyl-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl)sulfanyl]methyl}-1,3-thiazol-2-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

80 mg (0.17 mmol) of the compound from Example 13 were dissolved in 1.7 ml of dioxane, and 0.33 ml of a 1N aqueous sodium hydroxide solution were added. The reaction mixture was stirred at 50° C. for 3 h. 0.36 ml of 1N hydrochloric acid was then added to the mixture, and the resulting precipitate was filtered off, washed with water and dried.

Workup

  1. filtrationthe resulting precipitate was filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-0c0e8def21894c6fa4af5f0f2cf70ebb
Source dataset
uspto-grants-2013_12
Patent number
US08618119B2

Reaction notes

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