Hydrochloric Acid → 2,4-Diamino-6-ethyl-5-(3-(6-(3-carboxypropoxy)-2-methylquinolin-4-yloxy)propoxy)pyrimidine

HRID 40827Notes

Reaction equation

HRID 40827 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH2:25][CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])[CH:22]=3)[N:17]=[C:16]([CH3:33])[CH:15]=2)=[C:4]([CH2:34][CH3:35])[N:3]=1.[OH-].[K+].Cl>>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH:22]=3)[N:17]=[C:16]([CH3:33])[CH:15]=2)=[C:4]([CH2:34][CH3:35])[N:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 252629252,4-Diamino-6-ethyl-5-(3-(6-(3-ethoxycarbonylpropoxy)-2-methylquinolin-4-yloxy)propoxy)pyrimidine

Product 1

HCID 252629262,4-Diamino-6-ethyl-5-(3-(6-(3-carboxypropoxy)-2-methylquinolin-4-yloxy)propoxy)pyrimidineYield 84%

Conditions

Temperature
25 °C

Procedure

A suspension of the ethyl ester obtained in step (c) (0.314 g, 0.65 mmol) and aqueous KOH solution (10 equiv) was stirred at 25° C. overnight. The solution was neutralized by addition of dilute HCl. The precipitate formed was separated by filtration and dried in an oven at 80° C. to give a light yellow solid (0.2487 g, 84%). 1H NMR (400 MHz, DMSO-d6): 0.91 (3H, t, J=7.5 Hz), 1.98 (2H, m), 2.29 (4H, m), 2.41 (2H, t, J=7.2 Hz), 2.56 (3H, s), 3.86 (2H, t, J=5.5 Hz), 4.05 (2H, t, J=5.9 Hz), 4.40 (2H, t, J=5.3 Hz), 5.67 (2H, s), 6.24 (2H, s) 6.94 (1H, s), 7.33 (2H, m), 7.75 (1H, d, J=9.1 Hz).

Workup

  1. customThe precipitate formed
  2. customwas separated by filtration
  3. customdried in an oven at 80° C.

Sources & evidence

ORD record
ord-a6041321c32042889647d15a0998e0f2
Source dataset
uspto-grants-2013_09
Patent number
US08530491B2

Reaction notes

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