Diisopropylethylamine → 5-Methyl-7-(4-pyridyl)-2-(2-quinolin-2-yl-ethyl)-5H-pyrrolo[3,4-c]pyridine-1,3,6-trione

HRID 1752608Notes

Reaction equation

HRID 1752608 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([C:8]([OH:10])=O)[C:5]([C:11]([O:13]C)=O)=[C:4]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[C:3]1=[O:21].[NH2:22][CH2:23][CH2:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:1][N:2]1[C:3](=[O:21])[C:4]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[C:5]2[C:11](=[O:13])[N:22]([CH2:23][CH2:24][C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=3)[C:8](=[O:10])[C:6]2=[CH:7]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 101763222-(Quinolin-2-yl)ethan-1-amineHCID 904219011-Methyl-2-oxo-1,2-dihydro-3-(4-pyridyl)-4-methoxycarbonyl-pyridine-5-carboxylic acid

Product 1

HCID 862956345-Methyl-7-(4-pyridyl)-2-(2-quinolin-2-yl-ethyl)-5H-pyrrolo[3,4-c]pyridine-1,3,6-trioneYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-methyl-2-oxo-1,2-dihydro-3-(4-pyridyl)-4-methoxycarbonyl-pyridine-5-carboxylic acid (500 mg, 1.7 mmol, see Example b3)), 2-aminoethyl quinoline (358 mg, 2.0 mmol), PyBOP (1.2 g, 2.2 mmol) and DIPEA (671 mg, 5.2 mmol) in DCM (20 ml) was stirred at r.t. overnight. The solvent was removed, the residue was purified by column chromatography on silica gel (PE:EA=10:1) to give the title compound as a white solid (600 mg, 84%).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by column chromatography on silica gel (PE:EA=10:1)

Sources & evidence

ORD record
ord-d344aa0e8c3542bcb3c017ba0abf30bc
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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