Hydrochloric Acid → HCID 66749617, compound

HRID 2169979Notes

Reaction equation

HRID 2169979 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]([O-: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 86718251HCID 86718251, 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-carboxylate 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 NR (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-8ff75e8dd98844e38c202478ec5c10fa
Source dataset
uspto-grants-2015_06
Patent number
US09049878B2

Reaction notes

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