Sodium Hydroxide → 5-{1'-[(1-Cyclopropyl-4-methoxy-1h-indol-6-yl)carbonyl]-4-oxospiro[chroman-2,4'-piperidin]-6-yl}nicotinic acid sodium salt

HRID 420124Notes

Reaction equation

HRID 420124 reaction equation
[CH:1]1([N:4]2[C:12]3[C:7](=[C:8]([O:40][CH3:41])[CH:9]=[C:10]([C:13]([N:15]4[CH2:20][CH2:19][C:18]5([CH2:29][C:28](=[O:30])[C:27]6[C:22](=[CH:23][CH:24]=[C:25]([C:31]7[CH:32]=[N:33][CH:34]=[C:35]([CH:39]=7)[C:36]([OH:38])=[O:37])[CH:26]=6)[O:21]5)[CH2:17][CH2:16]4)=[O:14])[CH:11]=3)[CH:6]=[CH:5]2)[CH2:3][CH2:2]1.[OH-].[Na+:43]>O>[Na+:43].[CH:1]1([N:4]2[C:12]3[C:7](=[C:8]([O:40][CH3:41])[CH:9]=[C:10]([C:13]([N:15]4[CH2:16][CH2:17][C:18]5([CH2:29][C:28](=[O:30])[C:27]6[C:22](=[CH:23][CH:24]=[C:25]([C:31]7[CH:32]=[N:33][CH:34]=[C:35]([CH:39]=7)[C:36]([O-:38])=[O:37])[CH:26]=6)[O:21]5)[CH2:19][CH2:20]4)=[O:14])[CH:11]=3)[CH:6]=[CH:5]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 249636015-{1'-[(1-Cyclopropyl-4-methoxy-1H-indol-6-yl)carbonyl]-4-oxospiro[chroman-2,4'-piperidin]-6-yl}nicotinic acid

Product 1

HCID 249636025-{1'-[(1-Cyclopropyl-4-methoxy-1h-indol-6-yl)carbonyl]-4-oxospiro[chroman-2,4'-piperidin]-6-yl}nicotinic acid sodium salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-{1′-[(1-Cyclopropyl-4-methoxy-1H-indol-6-yl)carbonyl]-4-oxospiro[chroman-2,4′-piperidin]-6-yl}nicotinic acid (434 mg) was suspended in water (5 mL), and aqueous 1 N sodium hydroxide solution (0.865 mL) was added thereto and stirred at room temperature for 1 hour. The solution was purified by ODS reversed-phase column chromatography (water/methanol, gradient) to obtain the intended compound. 1H-NMR (400 MHz, DMSO-d6) δ: 8.90 (1H, d, J=1.7 Hz), 8.74 (1H, d, J=2.4 Hz), 8.29-8.27 (1H, m), 7.99-7.94 (2H, m), 7.29 (1H, d, J=3.2 Hz), 7.25-7.22 (2H, m), 6.59 (1H, s), 6.40 (1H, d, J=3.2 Hz), 4.49-4.04 (1H, br m), 3.87 (3H, s), 3.82-3.58 (1H, br m), 3.51-3.28 (3H, m), 2.95 (2H, s), 2.13-1.90 (2H, br m), 1.88-1.75 (2H, br m), 1.09-1.02 (2H, m), 0.95-0.90 (2H, m); MS [M+Na]+=574.

Workup

  1. customThe solution was purified by ODS reversed-phase column chromatography (water/methanol, gradient)
  2. customto obtain the intended compound

Sources & evidence

ORD record
ord-038d7a54577748b0b1f485c1bb4274b9
Source dataset
uspto-grants-2012_01
Patent number
US08093389B2

Reaction notes

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