Lithium Hydroxide → (4-Hydroxy-4-{4-[6-(6-trifluoromethyl-pyridin-3-ylamino)-pyridin-3-yl]-phenyl}-piperidin-1-yl)-acetic acid

HRID 76053Notes

Reaction equation

HRID 76053 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][N:6]1[CH2:11][CH2:10][C:9]([OH:35])([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[N:20][C:21]([NH:24][C:25]4[CH:26]=[N:27][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:30]=4)=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)C.[Li+].[OH-]>C1COCC1.CO.CN(C=O)C>[OH:35][C:9]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[N:20][C:21]([NH:24][C:25]4[CH:26]=[N:27][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:30]=4)=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7][N:6]([CH2:5][C:4]([OH:36])=[O:3])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57899083HCID 57899083, compound

Product 1

HCID 66615803(4-Hydroxy-4-{4-[6-(6-trifluoromethyl-pyridin-3-ylamino)-pyridin-3-yl]-phenyl}-piperidin-1-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 86634690HCID 86634690, compoundSolvent

Procedure

(4-Hydroxy-4-{4-[6-(6-trifluoromethyl-pyridin-3-ylamino)-pyridin-3-yl]-phenyl}-piperidin-1-yl)-acetic acid ethyl ester (137 mg, 0.27 mmol) was dissolved in THF/MeOH/DMF (3:1:1, 5 mL) and to the solution was added aqueous LiOH (4M, 1 mL). The mixture was stirred at room temperature for 18 hours, then the reaction mixture was filtered and purified by reverse-phase preparative HPLC to give the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.54 (qd, J=12.38, 4.29 Hz, 1H) 1.42 (qd, J=12.51, 4.42 Hz, 1H) 1.77 (td, J=14.08, 1.14 Hz, 2H) 2.78 (m, 1H) 2.98 (td, J=12.63, 2.27 Hz, 1H) 3.29 (s, 2H) 3.87 (dd, J=11.37, 2.27 Hz, 1H) 4.39 (ddd, J=12.69, 1.83, 1.64 Hz, 1H) 7.04 (d, J=8.59 Hz, 1H) 7.32 (d, J=8.34 Hz, 2H) 7.61 (d, J=8.34 Hz, 2H) 7.80 (d, J=8.84 Hz, 1H) 7.99 (dd, J=8.72, 2.65 Hz, 1H) 8.55-8.62 (m, 1H) 8.57 (d, J=2.53 Hz, 1H) 8.92 (d, J=2.27 Hz, 1H) 9.93 (s, 1H); (M+H)+473.3.

Workup

  1. filtrationthe reaction mixture was filtered
  2. custompurified by reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-e778f9c17e8f4c9fa0731ac9f2e0a671
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Reaction notes

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