Hydrochloric Acid → [2-Cyclopropyl-8-fluoro-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]acetic acid

HRID 1944371Notes

Reaction equation

HRID 1944371 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([CH3:32])=[C:9]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]3[CH:31]=[CH:30][CH:29]=[N:28]3)=[CH:23][CH:22]=1)[C:10]([CH:17]1[CH2:19][CH2:18]1)=[N:11]2.[OH-].[Li+].Cl>O1CCCC1.O>[CH:17]1([C:10]2[C:9]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([N:27]4[CH:31]=[CH:30][CH:29]=[N:28]4)=[CH:25][CH:26]=3)=[C:8]([CH3:32])[C:7]3[C:12](=[C:13]([F:16])[CH:14]=[CH:15][C:6]=3[O:5][CH2:4][C:3]([OH:33])=[O:2])[N:11]=2)[CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67456277[2-Cyclopropyl-8-fluoro-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]acetic acid methyl ester

Product 1

HCID 25097869[2-Cyclopropyl-8-fluoro-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]acetic acidYield 66.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [2-cyclopropyl-8-fluoro-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]acetic acid methyl ester (0.034 g) in tetrahydrofuran (0.19 mL) and water (0.19 mL) was treated with lithium hydroxide (0.037 g), and the resulting mixture was stirred at room temperature for 2 hours. The mixture was diluted with water, cooled to 0° C. and acidified by the addition of 1.0 M aqueous hydrochloric acid. The resulting precipitate was collected by filtration and dried to afford title compound as a pale pink solid (0.022 g).

Workup

  1. temperaturecooled to 0° C.
  2. filtrationThe resulting precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-36951be1345c4870904646915052e091
Source dataset
uspto-grants-2013_03
Patent number
US08394830B2

Reaction notes

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