Hydrochloric Acid → HCID 23701123, compound

HRID 545189Notes

Reaction equation

HRID 545189 reaction equation
C[O:2][C:3](=[O:43])[C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[C:12]3[C:39](=[CH:40][CH:41]=2)[O:38][C:15]2([CH2:20][CH2:19][N:18]([C:21]([C:23]4[CH:32]=[C:31]5[C:26]([CH:27]=[CH:28][N:29]=[C:30]5[CH:33]5[CH2:35][CH2:34]5)=[C:25]([O:36][CH3:37])[CH:24]=4)=[O:22])[CH2:17][CH2:16]2)[CH2:14][C:13]3=[O:42])[CH:7]=[N:6][CH:5]=1.[OH-].[Na+:45].Cl>CO.C1COCC1>[Na+:45].[CH:33]1([C:30]2[C:31]3[C:26](=[C:25]([O:36][CH3:37])[CH:24]=[C:23]([C:21]([N:18]4[CH2:17][CH2:16][C:15]5([CH2:14][C:13](=[O:42])[C:12]6[C:39](=[CH:40][CH:41]=[C:10]([C:8]7[CH:7]=[N:6][CH:5]=[C:4]([CH:9]=7)[C:3]([O-:43])=[O:2])[CH:11]=6)[O:38]5)[CH2:20][CH2:19]4)=[O:22])[CH:32]=3)[CH:27]=[CH:28][N:29]=2)[CH2:35][CH2:34]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57700077HCID 57700077, compound

Product 1

HCID 23701123HCID 23701123, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-{1′-[(1-Cyclopropyl-5-methoxy-isoquinolin-7-yl)carbonyl]-4-oxospiro[chroman-2,4′-piperidin]-6-yl}nicotinic acid methyl ester (1.80 g, 3.11 mmol) was suspended in MeOH (18 mL) and THF (9 mL), and 1N NaOH (9.34 mL) was added thereto. After stirred at room temperature for 5 h, 1N HCl aq. (6.23 mL) was added to the reaction mixture and the solvents was removed in vacuo. The residue was purified by ODS column chromatography (H2O/MeOH=100/0 to 60/40) to obtain the intended compound as a colorless solid. 1H-NMR (400 MHz, DMSO-d6) δ: 8.92 (1H, d, J=1.7 Hz), 8.76 (1H, d, J=2.4 Hz), 8.36 (1H, d, J=5.6 Hz), 8.31-8.28 (1H, m), 8.08 (1H, s), 8.00-7.96 (2H, m), 7.74 (1H, d, J=5.6 Hz), 7.23 (1H, d, J=9.3 Hz), 7.19 (1H, s), 4.41-4.26 (1H, br m), 4.01 (3H, s), 3.60-3.46 (1H, br m), 3.39-3.27 (2H, br m), 2.97-2.87 (1H, m), 2.95 (2H, s), 2.19-2.02 (1H, br m), 2.02-1.72 (3H, m), 1.15-1.04 (4H, m). ESI-MS [M+Na]+=586.

Workup

  1. customthe solvents was removed in vacuo
  2. customThe residue was purified by ODS column chromatography (H2O/MeOH=100/0 to 60/40)

Sources & evidence

ORD record
ord-94aada82a4e44c7fabbbd4669be0e21f
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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