Lithium Hydroxide → HCID 57899096, compound

HRID 1404243Notes

Reaction equation

HRID 1404243 reaction equation
C([O:3][C:4](=[O:36])[C:5](=[O:35])[N:6]1[CH2:11][CH2:10][CH:9]([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>[O:35]=[C:5]([N:6]1[CH2:7][CH2:8][CH:9]([C:12]2[CH:13]=[CH:14][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:33])([F:34])[F:32])=[CH:29][CH:30]=4)=[CH:22][CH:23]=3)=[CH:16][CH:17]=2)[CH2:10][CH2:11]1)[C:4]([OH:36])=[O:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66615852Oxo-(4-{4-[6-(6-trifluoromethyl-pyridin-3-ylamino)-pyridin-3-yl]-phenyl}-piperidin-1-yl)-acetic acid ethyl ester

Product 1

HCID 57899096HCID 57899096, compound

Reagents, catalysts & solvents 1

HCID 86634690HCID 86634690, compoundSolvent

Procedure

Oxo-(4-{4-[6-(6-trifluoromethyl-pyridin-3-ylamino)-pyridin-3-yl]-phenyl}-piperidin-1-yl)-acetic acid ethyl ester (229 mg, 0.46 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 1.41 (m, 1 H) 1.52 (m, 1 H) 1.76 (td, J=13.89, 1.52 Hz, 2 H) 2.72-2.81 (m, 1 H) 2.96 (td, J=12.63, 2.27 Hz, 1 H) 3.16 (d, J=5.31 Hz, 1 H) 3.85 (dd, J=11.37, 2.27 Hz, 1 H) 4.37 (ddd, J=12.69, 1.83; 1.64 Hz, 1 H) 7.03 (d, J=8.59 Hz, 1 H) 7.31 (d, J=8.34 Hz, 2 H) 7.60 (d, J=8.34 Hz, 2 H) 7.78 (d, J=8.84 Hz, 1 H) 7.98 (dd, J=8.72, 2.65 Hz, 1 H) 8.55 (d, J=2.53 Hz, 1 H) 8.58 (dd, J=8.59, 2.02 Hz, 1 H) 8.90 (d, J=2.27 Hz, 1 H) 9.91 (s, 1 H); MS (M+H)+ 471.2.

Workup

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

Sources & evidence

ORD record
ord-64bcb86507844bc3909269f40d61c227
Source dataset
uspto-grants-2014_12
Patent number
US08912208B2

Reaction notes

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