Lithium Hydroxide → HCID 69090495, compound

HRID 2376222Notes

Reaction equation

HRID 2376222 reaction equation
C([O:3][C:4](=[O:35])[C:5]([C:28]1[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=1)=[CH:6][C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[N:9]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[N:8]=1)C.[Li+].[OH-]>>[Cl:19][C:14]1[CH:13]=[C:12]([C:10]2[N:9]([C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[N:8]=[C:7]([CH:6]=[C:5]([C:28]3[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=3)[C:4]([OH:35])=[O:3])[CH:11]=2)[CH:17]=[CH:16][C:15]=1[Cl:18]

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 69198966HCID 69198966, compound

Product 1

HCID 69090495HCID 69090495, compoundYield 72.3%

Procedure

To a stirred solution containing 3-[5-(3,4-dichloro-phenyl)-1-(4-methoxy-phenyl)-1-H-pyrazol-3-yl]-2-m-tolyl-acrylic acid ethyl ester (Step B, 50 mg, 0.10 mmol) was added 2 mL LiOH (2 M). After 4 h at 50° C., the solvent was removed under reduced pressure and the residue was purified by silica gel chromatography with 5:95 MeOH/CH2Cl2 to afford 34 mg (72.3%) of the title compound. HPLC: Rt=10.65 (Method A). MS (ES+): mass calculated for C26H20Cl2N2O3, 478.09; m/z found 479.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.35 (t, J=8.0 Hz, 1H), 7.28-7.23 (m, 3H), 7.15-7.11 (m, 3H), 7.09 (d, J=2.0 Hz, 1H), 6.88-6.86 (m, 2H), 6.77 (dd, J=8.3, 2.0 Hz, 1H), 5.45 (s, 1H), 3.82 (s, 3H), 2.39 (s, 3H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue was purified by silica gel chromatography with 5:95 MeOH/CH2Cl2

Sources & evidence

ORD record
ord-96c8c3dbe7a64734aa52943df2a69a84
Source dataset
uspto-grants-2008_12
Patent number
US07465808B2

Reaction notes

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