Methanol → 2-(4-{6-Amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-propionic acid

HRID 2266713Notes

Reaction equation

HRID 2266713 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:32])[CH:6]([N:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[N:15][C:16]([NH2:31])=[C:17]([O:19][CH:20]([C:22]3[C:27]([Cl:28])=[CH:26][CH:25]=[C:24]([F:29])[C:23]=3[Cl:30])[CH3:21])[CH:18]=2)[CH:10]=[N:9]1)[CH3:7].C1COCC1.CO>O>[NH2:31][C:16]1[N:15]=[CH:14][C:13]([C:11]2[CH:10]=[N:9][N:8]([CH:6]([CH3:7])[C:5]([OH:32])=[O:4])[CH:12]=2)=[CH:18][C:17]=1[O:19][CH:20]([C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[C:24]([F:29])[C:23]=1[Cl:30])[CH3:21]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 67084570HCID 67084570, compound

Product 1

HCID 586591442-(4-{6-Amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-propionic acidYield 104.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of LiOH (34 mg, 1.4 mmol) in water (0.4 mL) was added to a solution of 2-(4-{6-Amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-propionic acid methyl ester (70 mg, 0.15 mmol) in a mixture THF (1.5 mL) and MeOH (0.4 mL). After stirring overnight, the reaction was partitioned between dichloromethane and half-saturated brine. A small amount of ethanol was added and the pH was adjusted to 7 with 1 M HCl. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over Na2SO4, filtered and concentrated by rotary evaporation to give 2-(4-{6-amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-propionic acid (69 mg, 100%).

Workup

  1. customthe reaction was partitioned between dichloromethane and half-saturated brine
  2. additionA small amount of ethanol was added
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with dichloromethane
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-c1bf0f64cfac4d7694b1e3be56bf8d1b
Source dataset
uspto-grants-2010_12
Patent number
US07858643B2

Reaction notes

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