Hydrochloric Acid → (5-{2-[(N-Cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid

HRID 554609Notes

Reaction equation

HRID 554609 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=2[CH2:21][N:22]([C:25]([CH:27]2[CH2:29][CH2:28]2)=[O:26])[CH2:23][CH3:24])[CH:10]=1.CO.[OH-].[Na+].Cl>C1COCC1>[CH:27]1([C:25]([N:22]([CH2:21][C:12]2[CH:13]=[C:14]([C:17]([F:20])([F:19])[F:18])[CH:15]=[CH:16][C:11]=2[C:9]2[CH:10]=[C:5]([CH2:4][C:3]([OH:30])=[O:2])[CH:6]=[N:7][CH:8]=2)[CH2:23][CH3:24])=[O:26])[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 67212307HCID 67212307, compound

Product 1

HCID 45138480(5-{2-[(N-Cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(5-{2-[(N-Cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid methyl ester (0.069 g, 0.16 mmol) was dissolved in THF (1 mL) and MeOH (0.8 mL) and treated with 1N aqueous NaOH (0.5 mL). The reaction was stirred at room temperature for 1 hour. The mixture was neutralized with 1N aqueous HCl and extracted twice with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated to give Compound 8.

Workup

  1. extractionextracted twice with CH2Cl2
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0bbe70d1583b4319a8a51bc85945ffb3
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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