4-Chlorobenzylamine → N-(4-Chlorobenzyl)-2-[(1R)-1-hydroxyethyl]-8-(4-morpholinylmethyl)-6-oxo-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide

HRID 1841534Notes

Reaction equation

HRID 1841534 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7](I)[CH:8]=[C:9]([CH2:12][N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:20](OCC)=[O:21].[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH2:31])=[CH:28][CH:27]=1>>[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH:31][C:20]([C:3]2[C:2](=[O:1])[C:11]3[C:6]4=[C:7]([CH:4]=[C:3]([C@H:2]([OH:1])[CH3:11])[N:5]4[CH:4]=2)[CH:8]=[C:9]([CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:10]=3)=[O:21])=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469655HCID 178469655, compound

Product 1

HCID 491965N-(4-Chlorobenzyl)-2-[(1R)-1-hydroxyethyl]-8-(4-morpholinylmethyl)-6-oxo-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide

Conditions

Temperature
190 °C

Procedure

To a flask containing ethyl 4-hydroxy-8-iodo-6-(4-morpholinylmethyl)-3-quinolinecarboxylate of Preparation 25 (3.11 g) is added 4-chlorobenzylamine (8.0 mL). The mixture is degassed under reduced pressure. The mixture is placed under an argon atmosphere and is heated at 190° C. for 3 h. The reaction is cooled to room temperature. The excess benzylamine is removed by high vacuum distillation. The residue is crystallized from acetonitrile:methanol (1:1, 800 mL) to yield 3.08 g of the title compound as a white solid.

Workup

  1. additionTo a flask containing
  2. customThe mixture is degassed under reduced pressure
  3. temperatureThe reaction is cooled to room temperature
  4. customThe excess benzylamine is removed by high vacuum distillation
  5. customThe residue is crystallized from acetonitrile:methanol (1:1, 800 mL)

Sources & evidence

ORD record
ord-16145a0404d741c7bbfa04357b54dd97
Source dataset
uspto-grants-2004_01
Patent number
US06683181B2

Reaction notes

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