Lithium Hydroxide → HCID 22171008, compound

HRID 2376228Notes

Reaction equation

HRID 2376228 reaction equation
C([O:3][C:4](=[O:36])[CH:5]([C:29]1[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=1)[CH2:6][C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][CH2:19][CH:20]=[CH2:21])=[CH:14][CH:13]=2)[N:9]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[N:8]=1)C.[Li+].[OH-]>C1COCC1.O>[CH2:19]([NH:18][C:15]1[CH:14]=[CH:13][C:12]([C:10]2[N:9]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)[N:8]=[C:7]([CH2:6][CH:5]([C:29]3[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=3)[C:4]([OH:36])=[O:3])[CH:11]=2)=[CH:17][CH:16]=1)[CH:20]=[CH2:21]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 23568905HCID 23568905, compound

Product 1

HCID 22171008HCID 22171008, compoundYield 77.5%

Reagents, catalysts & solvents 1

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

Procedure

To a solution of 3-[5-(4-allylamino-phenyl)-1-p-tolyl-1H-pyrazol-3-yl]-2-m-tolyl-propionic acid ethyl ester (90 mg, 0.2 mmol) was added LiOH (14 mg, 0.58 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 desired compound (70 mg, 77 %). MS (ESI): mass calculated for C29H29N3O2, 451.23; m/z found, 452.6 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.21-7.03 (m, 8H), 6.93 (d, J=8.8, 2H), 6.26 (s, 1H), 5.88-5.83 (m, 1H), 5.29-5.24 (m, 2H), 4.06 (dd, J=10.4, 5.1 Hz, 1H), 3.79(d, J=6.3 Hz, 2H), 3.54 (dd, J=15.0, 10.4 Hz, 1H), 3.09 (dd, J=15.0 5.1 Hz, 1H), 2.33 (s, 3H), 2.32 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-3ec9bd2de01e4b33ab19b1b18a914915
Source dataset
uspto-grants-2008_12
Patent number
US07465808B2

Reaction notes

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