Hydrochloric Acid → HCID 66749617, compound

HRID 1467133Notes

Reaction equation

HRID 1467133 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][CH2:13][C:14]([NH:17][C:18](=[O:31])[C:19]2[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH2:28][CH2:29][OH:30])[CH:20]=2)([CH3:16])[CH3:15])[N:5]=[C:4]([CH3:32])[C:3]=1[C:33]([OH:35])=[O:34].[ClH:36]>CCO>[ClH:36].[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][CH2:13][C:14]([NH:17][C:18](=[O:31])[C:19]2[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH2:28][CH2:29][OH:30])[CH:20]=2)([CH3:15])[CH3:16])[N:5]=[C:4]([CH3:32])[C:3]=1[C:33]([OH:35])=[O:34]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54588614HCID 54588614, compound

Product 1

HCID 66749617HCID 66749617, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred suspension of 4-amino-5-(2-(3-(2-hydroxyethoxy)-5-methoxybenzamido)-2-methylpropoxy)-2-methylquinoline-3-carboxylic acid (Example 38, 263 mg, 0.544 mmol) in EtOH (2 mL) was added HCl in EtOH (1.25 N, 479 uL, 1.1 equiv.). The mixture was stirred at room temperature until it became a clear solution (0.5 h). The solution was concentrated under reduced pressure to give the title compound as a white solid, which was further purified by re-crystallization from EtOH/H2O and dried under vacuum overnight (248 mg, 87%). 1H NMR (400 MHz, DMSO-d6) δ 1.51 (s, 6H), 2.80 (s, 3H), 3.68 (t, J=5.2 Hz, 2H), 3.74 (s, 3H), 3.97 (t, J=5.2 Hz, 1H), 4.53 (s, 2H), 6.59 (s, 1H), 6.92 (s, 1H), 6.94 (s, 1H), 7.27 (d, J=8.0 Hz, 1H), 7.57 (d, J=8.4 Hz, 1H), 7.86 (t, J=8.4 Hz, 1H), 8.03 (s, 1H), 9.40 (s, 1H), 9.98 (s, 1H), 484 (MH+-HCl).

Workup

  1. customa clear solution (0.5 h)
  2. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b87616bf6ad04bea9124032336bbca60
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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