Hydrochloric Acid → 1-(4'-{3-Methyl-4-[6-(2-methyl-phenyl)-pyridin-2-ylamino]-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid

HRID 45604Notes

Reaction equation

HRID 45604 reaction equation
C([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[NH:27][C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=5[CH3:40])[N:29]=4)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])C.[Li+].[OH-].Cl>CO>[CH3:26][C:23]1[C:22]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])[N:29]=2)=[C:21]([C:18]2[CH:19]=[CH:20][C:15]([C:12]3[CH:11]=[CH:10][C:9]([C:6]4([C:4]([OH:5])=[O:3])[CH2:8][CH2:7]4)=[CH:14][CH:13]=3)=[CH:16][CH:17]=2)[O:25][N:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 70816980HCID 70816980, compound

Product 1

HCID 627050191-(4'-{3-Methyl-4-[6-(2-methyl-phenyl)-pyridin-2-ylamino]-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(4′-{3-Methyl-4-[6-(2-methyl-phenyl)-pyridin-2-ylamino]-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid ethyl ester (0.015 g, 0.03 mmol) was dissolved in MeOH (3 mL) and treated with LiOH (0.50 mL of 1.0 N aq solution) and stirred at room temperature for 72 hrs. The resulting mixture was neutralized with HCl (0.50 mL of 1.0 N aq solution) and purified on reverse-phase preparative HPLC to afford the title compound.

Workup

  1. custompurified on reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-529426c0ac4f4494b77964e80c805695
Source dataset
uspto-grants-2013_09
Patent number
US08541587B2

Reaction notes

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