2-(Quinolin-2-yl)ethan-1-amine → 7-Chloro-5-(4-methoxy-benzyl)-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione

HRID 1752603Notes

Reaction equation

HRID 1752603 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][NH2:13].[Cl:14][C:15]1[C:16](=[O:36])[N:17]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[CH:18]=[C:19]([CH2:25]Cl)[C:20]=1[C:21](OC)=[O:22]>CCO>[Cl:14][C:15]1[C:16](=[O:36])[N:17]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[CH:18]=[C:19]2[CH2:25][N:13]([CH2:12][CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)[C:21](=[O:22])[C:20]=12

Participants

4

Reactant 2

HCID 101763222-(Quinolin-2-yl)ethan-1-amineHCID 904218061-(4-Methoxybenzyl)-2-oxo-1,2-dihydro-3-chloro-4-methoxycarbonyl-5-chloromethyl-pyridine

Product 1

HCID 904218377-Chloro-5-(4-methoxy-benzyl)-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dioneYield 53.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-(quinolin-2-yl)ethanamine (48.4 mg, 0.281 mmol, see Example a1)), methyl 3-chloro-5-(chloromethyl)-1-(4-methoxybenzyl)-2-oxo-1,2-dihydropyridine-4-carboxylate (100 mg, 0.281 mmol) and TEA (0.117 ml, 0.842 mmol) were dissolved in EtOH (3.0 ml) in a 5 ml microwave reaction vial. The suspension was heated in a Biotage microwave at about 100° C. for about 20 min. After cooling, it was verified by LC-MS that the reaction was almost completed. The solution was concentrated to dryness and recrystallized from EtOH to give the title compound (69 mg, 0.150 mmol, 53.4% yield) as a yellow solid.

Workup

  1. temperatureAfter cooling
  2. concentrationThe solution was concentrated to dryness
  3. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-dbfeecda78654e4389abdcd95919883c
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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