Water → HCID 131736839, compound

HRID 1486952Notes

Reaction equation

HRID 1486952 reaction equation
[OH-:1].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:14]([O:16]CC)=[O:15])=[C:7]2[NH:19][C@@H:20]1[CH2:24][CH2:23][C@@H:22]([O:25][CH3:26])[CH2:21]1.[Br:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[N:34]=[CH:33][C:32]([C:38]([O:40]CC)=[O:39])=[C:31]2[NH:43][C@H:44]1[CH2:48][CH2:47][C@H:46]([O:49][CH3:50])[CH2:45]1.[OH2:51]>CO>[O:1]=[O+:51][O-:15].[Br:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[N:34]=[CH:33][C:32]([C:38]([OH:40])=[O:39])=[C:31]2[NH:43][C@@H:44]1[CH2:48][CH2:47][C@@H:46]([O:49][CH3:50])[CH2:45]1.[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:14]([OH:16])=[O:15])=[C:7]2[NH:19][C@H:20]1[CH2:24][CH2:23][C@H:22]([O:25][CH3:26])[CH2:21]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 124137770HCID 124137770, compound

Product 1

HCID 131736839HCID 131736839, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2N Sodium hydroxide (150 mL) was added to a mixture of ethyl 6-bromo-4-[[(1R,3R)-3-methoxycyclopentyl]amino]quinoline-3-carboxylate: ethyl 6-bromo-4-[[(1S,3S)-3-methoxycyclopentyl]amino]quinoline-3-carboxylate (1:1 mixture) (18.6 g, 47.2 mmol) in MeOH (500 mL) and water (100 mL) and the resulting solution stirred for 15 h at ambient temperature. The mixture was concentrated under vacuum and the residue diluted with water (300 mL). The pH value of the solution was adjusted to 5 with 2N hydrochloric acid, the solids collected by filtration and dried in an oven under reduced pressure to afford the desired material (as a racemic mixture) (17.1 g) as a off-white solid. NMR Spectrum: 1H NMR (400 MHz, DMSO-d6) δ 1.60-1.71 (2H, m), 1.81-1.88 (1H, m), 1.96-2.62 (1H, m), 2.03-2.10 (2H, m), 3.21 (3H, s), 3.91-3.96 (1H, m), 4.51-4.72 (1H, m), 7.77 (1H, d), 7.93 (1H, d), 8.45 (1H, d), 8.85 (1H, s), 13.30 (1H, bs). Mass Spectrum: m/z (ES+)[M+H]+=365.2.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additionthe residue diluted with water (300 mL)
  3. filtrationthe solids collected by filtration
  4. customdried in an oven under reduced pressure

Sources & evidence

ORD record
ord-6cdf0557f9094653a370533ff5a16b6b
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

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