5-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid (6-piperazin-1-ylmethyl-pyridin-3-yl)-amide → 5-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid (5-{[(2-dimethylamino-ethyl)-methyl-amino]-methyl}-pyridin-2-yl)-amide

HRID 2409771Notes

Reaction equation

HRID 2409771 reaction equation
N1(CC2N=CC([NH:14][C:15]([C:17]3[CH:18]=[CH:19][C:20]([C:27]4[C:32]([Cl:33])=[C:31]([O:34][CH3:35])[CH:30]=[C:29]([O:36][CH3:37])[C:28]=4[Cl:38])=[C:21]4[C:26]=3[N:25]=[CH:24][CH:23]=[CH:22]4)=[O:16])=CC=2)CCNCC1.N[C:40]1[N:45]=[CH:44][C:43]([CH2:46][N:47]([CH3:53])[CH2:48][CH2:49][N:50]([CH3:52])[CH3:51])=[CH:42][CH:41]=1>C(Cl)Cl.CO>[CH3:51][N:50]([CH3:52])[CH2:49][CH2:48][N:47]([CH2:46][C:43]1[CH:42]=[CH:41][C:40]([NH:14][C:15]([C:17]2[CH:18]=[CH:19][C:20]([C:27]3[C:28]([Cl:38])=[C:29]([O:36][CH3:37])[CH:30]=[C:31]([O:34][CH3:35])[C:32]=3[Cl:33])=[C:21]3[C:26]=2[N:25]=[CH:24][CH:23]=[CH:22]3)=[O:16])=[N:45][CH:44]=1)[CH3:53]

Participants

4

Reactant 2

HCID 592929145-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid (6-piperazin-1-ylmethyl-pyridin-3-yl)-amideHCID 592929455-({[2-(Dimethylamino)ethyl](methyl)amino}methyl)pyridin-2-amine

Product 1

HCID 445144635-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid (5-{[(2-dimethylamino-ethyl)-methyl-amino]-methyl}-pyridin-2-yl)-amide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared in analogy to the procedure described in Step 14.1 but using 5-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid (6-piperazin-1-ylmethyl-pyridin-3-yl)-amide (Exam pie 170), N-(6-amino-pyridin-3-ylmethyl)-N,N′,N′-trimethyl-ethane-1,2-diamine (prepared as described in Example 26 but using N,N,N′-trimethyl-ethane-1,2-diamine in Step 26.2), and stirring the reaction mixture for 14 h at rt. Title compound: ESI-MS: 568.0 [M+H]+; TLC: Rf=0.15 (DCM/MeOH, 9:1).

Workup

  1. customThe title compound was prepared in analogy to the procedure

Sources & evidence

ORD record
ord-a7debaec2ce5430a993dc58479d2aefb
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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