Hydrochloric Acid → HCID 11156490, compound

HRID 1171452Notes

Reaction equation

HRID 1171452 reaction equation
C([O:3][C:4](=[O:38])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([S:20][C:21]3[N:25]([CH3:26])[C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[N:23][N:22]=3)=[CH:16][C:15]=2[O:34][CH2:35][CH2:36][CH3:37])=[CH:8][CH:7]=1)C.C(=O)([O-])[O-].[K+].[K+].Cl>CO>[CH2:27]([C:24]1[N:25]([CH3:26])[C:21]([S:20][C:17]2[CH:18]=[CH:19][C:14]([CH2:13][NH:12][C:9]3[CH:8]=[CH:7][C:6]([CH2:5][C:4]([OH:38])=[O:3])=[CH:11][CH:10]=3)=[C:15]([O:34][CH2:35][CH2:36][CH3:37])[CH:16]=2)=[N:22][N:23]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 58828971HCID 58828971, compound

Product 1

HCID 11156490HCID 11156490, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of {4-[4-(5-heptyl-4-methyl-4H-[1,2,4]-triazol-3-ylsulfanyl)-2-propoxybenzylamino]phenyl}acetic acid ethyl ester obtained in Example 31 (0.7 g, 2.39 mmol), 2M aqueous potassium carbonate (9 ml) in methanol (20 ml) is heated under reflux for 3 hours. The reaction medium is acidified at room temperature with a 2N hydrochloric acid solution to pH 5. The desired product is extracted by addition of ethyl acetate. The organic phase is washed with water, dried over magnesium sulfate. After evaporation of the solvents, 0.592 g (89%) of the expected compound are recovered in the form of a yellow amorphous solid.

Workup

  1. temperatureunder reflux for 3 hours
  2. extractionThe desired product is extracted by addition of ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvents, 0.592 g (89%) of the expected compound
  6. customare recovered in the form of a yellow amorphous solid

Sources & evidence

ORD record
ord-3ce5377172094082970dc3e974b0fb19
Source dataset
uspto-grants-2010_11
Patent number
US07829588B2

Reaction notes

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