Methanol → HCID 71294051, compound

HRID 240719Notes

Reaction equation

HRID 240719 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:20]([NH:22][N:23]3[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][O:31]C(=O)C)[CH2:25][CH2:24]3)=[O:21])[CH:11]=[N:12][C:13]=2[O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:4][CH:3]=1.C1COCC1.CO.[OH-].[Li+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:20]([NH:22][N:23]3[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][OH:31])[CH2:25][CH2:24]3)=[O:21])[CH:11]=[N:12][C:13]=2[O:14][CH2:15][C:16]([F:18])([F:19])[F:17])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 71294296HCID 71294296, compound

Product 1

HCID 71294051HCID 71294051, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetic acid 2-(4-{[5-(4-chloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-pyridine-3-carbonyl]-amino}-piperazin-1-yl)-ethyl ester (100 mg, 200 μmol) was combined with THF (2 mL), methanol (1 mL) and water (1 mL) to give a light yellow solution. Lithium hydroxide (14.3 mg, 599 μmol) was added and the mixture was stirred for 1 h at room temperature. Subsequently the reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography (silica gel, 12 g, 0% to 100% ethyl acetate in n-heptane) to give the title compound (32 mg, 35%) as light yellow solid; MS (EI) 459.2 (M+H)+.

Workup

  1. customto give a light yellow solution
  2. concentrationSubsequently the reaction mixture was concentrated in vacuo
  3. customthe residue was purified by flash chromatography (silica gel, 12 g, 0% to 100% ethyl acetate in n-heptane)

Sources & evidence

ORD record
ord-280f172a6e8145d5a6c762779c225fa8
Source dataset
uspto-grants-2014_02
Patent number
US08648099B2

Reaction notes

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