HCID 10407118, compound → HCID 9795552, compound

HRID 1455502Notes

Reaction equation

HRID 1455502 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[C:22]([C:23]([OH:25])=[O:24])=[CH:21][C:20]2[C:15](=[CH:16][C:17]([O:26][CH3:27])=[CH:18][CH:19]=2)[N:14]=1)=O)(C)(C)C>Cl.O1CCOCC1>[NH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[C:22]([C:23]([OH:25])=[O:24])=[CH:21][C:20]2[C:15](=[CH:16][C:17]([O:26][CH3:27])=[CH:18][CH:19]=2)[N:14]=1

Participants

3

Reactant 1

HCID 10407118HCID 10407118, compound

Product 1

HCID 9795552HCID 9795552, compound

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A suspension of 2-(3-tert-Butoxycarbonylamino-propylamino)-7-methoxy-quinoline-3-carboxylic acid (30 mg, 0.08 mmol) in dry 4N HCl/1,4-Dioxane (1 ml) solution was heated at reflux for 5 days. After evaporating the solvent, the residue was recrystallized from methanol and diethyl ether to give 2-(3-Amino-propylamino)-7-methoxy-quinoline-3-carboxylic acid as the white crystal; 19.3 mg (88%). 1H NMR (400 MHz, DMSO-d6) ppm 1.91 (m, 2H), 2.90 (t, 2H, J=7.3 Hz), 3.56 (m, 2H), 3.83 (s, 3H), 6.74 (dd, 1H, J=2.4, 8.6 Hz), 6.88 (d, 1H, J=2.4 Hz), 7.55 (d, 1H, J=8.6 Hz), 8.24 (br, 1H), 8.37 (s, 1H), 10.38 (br, 1H). LC/MS: m/z 276 (M+1)+, 274 (M−1)−.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 days
  3. customAfter evaporating the solvent
  4. customthe residue was recrystallized from methanol and diethyl ether

Sources & evidence

ORD record
ord-fb487880ab9245e0a04026b1420ec71c
Source dataset
uspto-grants-2009_01
Patent number
US07482455B2

Reaction notes

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