2-{4-[4-(4-Methoxy-benzylamino)-3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl]-phenyl}-2-methyl-propionitrile → 2-[4-(4-Amino-3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-phenyl]-2-methyl-propionitrile

HRID 1670489Notes

Reaction equation

HRID 1670489 reaction equation
COC1C=CC(C[NH:8][C:9]2[C:18]3[N:19]([CH3:34])[C:20](=[O:33])[N:21]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([CH3:32])([CH3:31])[C:29]#[N:30])=[CH:24][CH:23]=4)[C:17]=3[C:16]3[CH:15]=[C:14]([C:35]4[CH:36]=[N:37][C:38]5[C:43]([CH:44]=4)=[CH:42][CH:41]=[CH:40][CH:39]=5)[CH:13]=[CH:12][C:11]=3[N:10]=2)=CC=1>C(O)(C(F)(F)F)=O>[NH2:8][C:9]1[C:18]2[N:19]([CH3:34])[C:20](=[O:33])[N:21]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([CH3:32])([CH3:31])[C:29]#[N:30])=[CH:24][CH:23]=3)[C:17]=2[C:16]2[CH:15]=[C:14]([C:35]3[CH:36]=[N:37][C:38]4[C:43]([CH:44]=3)=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

3

Reactant 1

HCID 536303572-{4-[4-(4-Methoxy-benzylamino)-3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl]-phenyl}-2-methyl-propionitrile

Product 1

HCID 119791562-[4-(4-Amino-3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-phenyl]-2-methyl-propionitrile

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

110 mg (0.182 mmol) of 2-{-4-[4-(4-methoxy-benzylamino)-3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl]-phenyl}-2-methyl-propionitrile (Example 109a) in 1.1 ml TFA are stirred at rt for 24 h and then at 35° C. for 5 h. The reaction mixture is purified by preparative HPLC to provide the title compound as an off-white solid. ES-MS: 485 (M+H)+; analytical HPLC: tret=2.86 minutes (Grad 1).

Workup

  1. customThe reaction mixture is purified by preparative HPLC

Sources & evidence

ORD record
ord-8d9b7821cf38475e885e5d33014eced0
Source dataset
uspto-grants-2011_08
Patent number
US07994170B2

Reaction notes

Loading…