Hydrochloric Acid → HCID 66811846, compound

HRID 1097419Notes

Reaction equation

HRID 1097419 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:34]=[C:14]3[N:15]=[CH:16][CH:17]=[C:18]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH:26]([F:28])[F:27])=[C:21]([O:29][CH2:30][CH:31]5[CH2:33][CH2:32]5)[CH:20]=4)[N:13]3[N:12]=2)=[CH:7][N:6]=1)=[O:4].[Li+].[OH-].Cl>CO>[CH:31]1([CH2:30][O:29][C:21]2[CH:20]=[C:19]([C:18]3[N:13]4[N:12]=[C:11]([C:8]5[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=5)[N:34]=[C:14]4[N:15]=[CH:16][CH:17]=3)[CH:24]=[CH:23][C:22]=2[O:25][CH:26]([F:27])[F:28])[CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66812045HCID 66812045, compound2×

Product 1

HCID 66811846HCID 66811846, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In aqueous MeOH, dissolved was 5-[7-{3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl}-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]pyridine-2-carboxylic acid methyl ester (Compound 138) (0.05 g, 0.11 mmol), and LiOH (0.013 g, 0.32 mmol) was slowly added thereto. By using dilute HCl, pH of the reaction mixture was adjusted to 4˜5. The mixture was extracted three times with EA, and the extract was washed twice with brine, dried over MgSO4, filtered, and evaporated under reduced pressure to remove solvent. The mixture was purified via silica gel column chromatography (MeOH) to obtain desired compound, 5-[7-{3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl}-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]pyridine-2-carboxylic acid (Compound 137) (0.017 g, 35%).

Workup

  1. additionwas slowly added
  2. extractionThe mixture was extracted three times with EA
  3. washthe extract was washed twice with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto remove solvent
  8. customThe mixture was purified via silica gel column chromatography (MeOH)

Sources & evidence

ORD record
ord-f3ad95dba5ca44a28371b3b9f515a243
Source dataset
uspto-grants-2012_03
Patent number
US08143262B2

Reaction notes

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