Sodium Hydroxide → (4-{[{4-[(4-butylphenyl)ethynyl]benzyl}(1H-pyrazol-4-ylcarbonyl)amino]methyl}phenoxy)acetic acid

HRID 733585Notes

Reaction equation

HRID 733585 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:40]=[CH:39][C:16]([CH2:17][N:18]([CH2:26][C:27]3[CH:38]=[CH:37][C:30]([O:31][CH2:32][C:33]([O:35]C)=[O:34])=[CH:29][CH:28]=3)[C:19]([C:21]3[CH:22]=[N:23][NH:24][CH:25]=3)=[O:20])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>CO.C1COCC1>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:40]=[CH:39][C:16]([CH2:17][N:18]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([O:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:37][CH:38]=3)[C:19]([C:21]3[CH:25]=[N:24][NH:23][CH:22]=3)=[O:20])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57841328methyl (4-{[{4-[(4-butylphenyl)ethynyl]benzyl}(1H-pyrazol-4-ylcarbonyl)amino]methyl}phenoxy)acetate

Product 1

HCID 11214580(4-{[{4-[(4-butylphenyl)ethynyl]benzyl}(1H-pyrazol-4-ylcarbonyl)amino]methyl}phenoxy)acetic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The titled compound was prepared following the procedure F using methyl (4-{[{4-[(4-butylphenyl)ethynyl]benzyl}(1H-pyrazol-4-ylcarbonyl)amino]methyl}phenoxy)acetate and NaOH 1N in the presence of MeOH/THF as a white powder (30%). 1H NMR (MeOD, 300 MHz) δ 7.76 (m, 2H), 7.45 (m, 4H), 7.17 (m, 6H), 6.88 (m, 2H), 4.64 (s, 2H), 3.94 (s, 4H), 2.59 (t J=7.7 Hz, 2H), 1.57 (m, 2H), 1.33 (m, 2H), 0.90 (t, J=7.3 Hz, 3H). HPLC, Rt: 4.62 min (Purity: 88%).

Sources & evidence

ORD record
ord-f7b03b164eb34f6285d10083964a4391
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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