Diisopropylethylamine → 2-(3-Amino-2-methoxyprop-1-ylamino)-4-methoxyquinoline

HRID 430083

Reaction equation

HRID 430083 reaction equation
Cl[C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:14][O:15][CH:16]([CH2:19][NH2:20])[CH2:17][NH2:18].CCN(C(C)C)C(C)C>CO>[NH3:3].[NH2:18][CH2:17][CH:16]([O:15][CH3:14])[CH2:19][NH:20][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 99111382-Methoxypropane-1,3-diamineHCID 123691662-Chloro-4-methoxyquinoline

Product 2

HCID 222AmmoniaHCID 183536912-(3-Amino-2-methoxyprop-1-ylamino)-4-methoxyquinolineYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-chloro-4-methoxyquinoline (1.75 g, 0.00903 mol), 2-methoxy-1,3-propanediamine, bis(trifluoroacetate) (6.00 g, 0.0181 mol) and N,N′-diisopropylethylamine (20 ml) was stirred for 18 h at 110° C. in a sealed reaction tube. After cooling the two phase mixture was diluted in methanol, concentrated onto silica, and then purified by silica gel chromatography (100% dichloromethane, 5%, 10% then 20% (10% 880 aqueous ammonia in methanol) in dichloromethane) to give the title compound as a yellow oil (0.86g, 36%). δH (CD3OD) 3.26-3.56 (4H, m, 2CH2), 3.46 (3H, s, CHOCH3), 3.40-3.60 (1H, m, CHOCH3), 4.02 (3H, s, COCH3), 6.10 (1H, s, 3-H), 7.00-7.81 (4H, m, ArH). MS (ES+) 262 (M+H).

Workup

  1. temperatureAfter cooling the two phase mixture
  2. concentrationconcentrated onto silica
  3. custompurified by silica gel chromatography (100% dichloromethane, 5%, 10%

Sources & evidence

ORD record
ord-5802f5090b4446e7803f2b4e2b70c668
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Linked notes

Loading…