Sodium Hydroxide → sodium 5-{1'-[(8-Cyclopropyl-4-methoxy-quinolin-2-yl)carbonyl]-4-oxospiro[chroman-2,4'-piperidin]-6-yl}nicotinate

HRID 545191Notes

Reaction equation

HRID 545191 reaction equation
[CH:1]1([C:4]2[CH:5]=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[C:11]([C:14]([N:16]2[CH2:21][CH2:20][C:19]4([CH2:30][C:29](=[O:31])[C:28]5[C:23](=[CH:24][CH:25]=[C:26]([C:32]6[CH:33]=[N:34][CH:35]=[C:36]([CH:40]=6)[C:37]([OH:39])=[O:38])[CH:27]=5)[O:22]4)[CH2:18][CH2:17]2)=[O:15])[CH:10]=[C:9]3[O:41][CH3:42])[CH2:3][CH2:2]1.[OH-].[Na+:44]>O>[CH:1]1([C:4]2[CH:5]=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[C:11]([C:14]([N:16]2[CH2:21][CH2:20][C:19]4([CH2:30][C:29](=[O:31])[C:28]5[C:23](=[CH:24][CH:25]=[C:26]([C:32]6[CH:33]=[N:34][CH:35]=[C:36]([CH:40]=6)[C:37]([O-:39])=[O:38])[CH:27]=5)[O:22]4)[CH2:18][CH2:17]2)=[O:15])[CH:10]=[C:9]3[O:41][CH3:42])[CH2:3][CH2:2]1.[Na+:44]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 160405075-{1'-[(8-Cyclopropyl-4-methoxy-quinolin-2-yl)carbonyl]-4-oxospiro[chroman-2,4'-piperidin]-6-yl}nicotinic acid

Product 1

HCID 23663305sodium 5-{1'-[(8-Cyclopropyl-4-methoxy-quinolin-2-yl)carbonyl]-4-oxospiro[chroman-2,4'-piperidin]-6-yl}nicotinate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-{1′-[(8-Cyclopropyl-4-methoxy-quinolin-2-yl)carbonyl]-4-oxospiro[chroman-2,4′-piperidin]-6-yl}nicotinic acid (3.53 g, 6.26 mmol) was suspended in H2O (35 mL) and 1N NaOH (6.26 mL) was added at 0° C. The resulted solution was purified by ODS column chromatography (eluent: H2O/MeOH=10/0 to 40/60) to afford sodium 5-{1′-[(8-Cyclopropyl-4-methoxy-quinolin-2-yl)carbonyl]-4-oxospiro[chroman-2,4′-piperidin]-6-yl}nicotinate as a colorless solid. 1H-NMR (400 MHz, DMSO-d6) δ: 8.91 (1.0H, d, J=1.7 Hz), 8.74 (1.0H, d, J=2.4 Hz), 8.30-8.28 (1.0H, m), 7.98-7.93 (3.0H, m), 7.49 (1.0H, dd, J=8.5, 7.3 Hz), 7.27-7.23 (2.0H, m), 7.20 (1.0H, s), 4.43-4.30 (1.0H, m), 4.07 (3.0H, s), 3.94-3.85 (1.0H, m), 3.61-3.46 (1.0H, m), 3.35-3.27 (1.0H, m), 3.12-3.03 (1.0H, m), 2.97 (2.0H, s), 2.17-2.06 (1.0H, m), 2.04-1.79 (3.0H, m), 1.15-1.03 (2.0H, m), 0.89-0.69 (2.0H, m). MS [M+Na]+=586.

Workup

  1. customThe resulted solution was purified by ODS column chromatography (eluent: H2O/MeOH=10/0 to 40/60)

Sources & evidence

ORD record
ord-37ae115dc19843cc818aae16ad8a7cd3
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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