Sodium Hydroxide → 5-(1'-{[3,5-Diethoxy-4-(1-methyl-1h-pyrazol-4-yl)phenyl]carbonyl}-4-oxospiro[chroman-2,4'-piperidin]-6-yl)pyridine-3-carboxylic acid sodium salt

HRID 1096899Notes

Reaction equation

HRID 1096899 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:19]([N:21]2[CH2:26][CH2:25][C:24]3([CH2:35][C:34](=[O:36])[C:33]4[C:28](=[CH:29][CH:30]=[C:31]([C:37]5[CH:38]=[C:39]([C:43]([OH:45])=[O:44])[CH:40]=[N:41][CH:42]=5)[CH:32]=4)[O:27]3)[CH2:23][CH2:22]2)=[O:20])[CH:7]=[C:8]([O:16][CH2:17][CH3:18])[C:9]=1[C:10]1[CH:11]=[N:12][N:13]([CH3:15])[CH:14]=1)[CH3:2].[OH-].[Na+:47]>O>[Na+:47].[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:19]([N:21]2[CH2:26][CH2:25][C:24]3([CH2:35][C:34](=[O:36])[C:33]4[C:28](=[CH:29][CH:30]=[C:31]([C:37]5[CH:38]=[C:39]([C:43]([O-:45])=[O:44])[CH:40]=[N:41][CH:42]=5)[CH:32]=4)[O:27]3)[CH2:23][CH2:22]2)=[O:20])[CH:7]=[C:8]([O:16][CH2:17][CH3:18])[C:9]=1[C:10]1[CH:11]=[N:12][N:13]([CH3:15])[CH:14]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 249996275-(1'-{[3,5-Diethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl]carbonyl}-4-oxospiro[chroman-2,4'-piperidin]-6-yl)pyridine-3-carboxylic acid

Product 1

HCID 249996285-(1'-{[3,5-Diethoxy-4-(1-methyl-1h-pyrazol-4-yl)phenyl]carbonyl}-4-oxospiro[chroman-2,4'-piperidin]-6-yl)pyridine-3-carboxylic acid sodium salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(1′-{[3,5-Diethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl]carbonyl}-4-oxospiro[chroman-2,4′-piperidin]-6-yl)pyridine-3-carboxylic acid (285 mg) was suspended in water (6 mL), and aqueous 1 N sodium hydroxide solution (0.624 mL) was added to it at room temperature, and stirred for 1 hour. The reaction liquid was purified through ODS reversed-phase chromatography (water/methanol) to obtain the title compound. 1H-NMR (400 MHz, DMSO-d6) δ: 8.90-8.87 (1.0H, m), 8.74-8.72 (1.0H, m), 8.28-8.26 (1.0H, m), 8.05 (1.0H, s), 7.99-7.95 (2.0H, m), 7.93-7.92 (1.0H, m), 7.22 (1.0H, d, J=9.3 Hz), 6.69 (2.0H, s), 4.35-4.18 (1.0H, br m), 4.08 (4.0H, q, J=6.8 Hz), 3.86 (3.0H, s), 3.69-3.17 (3.0H, m), 2.93 (2.0H, s), 2.15-1.86 (2.0H, m), 1.85-1.74 (2.0H, m), 1.38 (6.0H, t, J=7.0 Hz). MS [M+Na]+=633.

Workup

  1. customThe reaction liquid
  2. customwas purified through ODS reversed-phase chromatography (water/methanol)

Sources & evidence

ORD record
ord-5419a13e831a47f3bf8cc43ddaaef119
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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