Lithium Hydroxide → HCID 44444856, compound

HRID 1823223Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:12]=[C:11]([CH:22]=[C:23]([C:27]3[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=3)[C:24]([OH:26])=[O:25])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(OC(=O)C(C1C=C(C)C=CC=1)=CC1C=C(C2C=CC(Cl)=C(Cl)C=2)N(C2C=CC(OC)=CC=2)N=1)C.[Li+].[OH-]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[N:12]=[C:11](/[CH:22]=[C:23](\[C:27]3[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=3)/[C:24]([OH:26])=[O:25])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Reactant 3

HCID 3939Lithium Hydroxide

HCID 69090495HCID 69090495, compound

HCID 69198966HCID 69198966, compound

Product 1

HCID 44444856HCID 44444856, compoundYield 72.3%

Procedure

3-[5-(3.4-Dichloro-phenyl)-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-2-m-tolyl-acrylic acid. 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

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

Sources & evidence

ORD record: ord-4bec015c19d94eeda87aa09e1aa2b229
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07037931B2

Reaction notes

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