Lithium Hydroxide → HCID 11754688, compound

HRID 2376226Notes

Reaction equation

HRID 2376226 reaction equation
C([O:3][C:4](=[O:33])[CH:5]([C:26]1[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=1)[CH2:6][C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)[N:9]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[N:8]=1)C.[Li+].[OH-]>C1COCC1.O>[Br:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[N:9]([C:19]3[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=3)[N:8]=[C:7]([CH2:6][CH:5]([C:26]3[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=3)[C:4]([OH:33])=[O:3])[CH:11]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 23568904HCID 23568904, compound

Product 1

HCID 11754688HCID 11754688, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 3-[5-(4-bromo-phenyl)-1-p-tolyl-1H-pyrazol-3-yl]-2-m-tolyl-propionic acid ethyl ester (100 mg, 0.2 mmol) was added LiOH (14 mg, 0.6 mmol, 3 equiv) in 2:1 THF/H2O (1 mL). After 3 h at 45° C., the mixture was purified by preparative reversed-phase HPLC (acetonitrile/water) to afford the title compound (66 mg, 79 %). HPLC: Rt=4.25 (Method A). MS (ESI): mass calculated for C26H23BrN2O2, 474.09; m/z found, 475/477 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.40 (d, J=8.5 Hz, 2H), 7.22 (d, J=7.6 Hz, 2H), 7.19-7.05 (m, 7H), 7.01 (d, J=8.5 Hz, 2H), 6.23 (s, 1H), 4.10 (dd, J=9.6, 5.5 Hz, 1H), 3.53 (dd, J=14.8, 9.6 Hz, 1H), 3.13 (dd, J=14.8, 5.5 Hz, 1H), 2.36 (s, 3H), 2.34 (s, 3H).

Workup

  1. customthe mixture was purified by preparative reversed-phase HPLC (acetonitrile/water)

Sources & evidence

ORD record
ord-863ed4ba0ae14e41b50e655894af8abb
Source dataset
uspto-grants-2008_12
Patent number
US07465808B2

Reaction notes

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