N-(3-cyclopropyl-4-((4-methylpiperazin-1-yl)methyl)phenyl)-3-iodo-4-methylbenzamide → 3-(cinnolin-4-ylethynyl)-N-{3-cyclopropyl-4-[(4-methylpiperazin-1-yl)methyl]phenyl}-4-methylbenzamide

HRID 1255941Notes

Reaction equation

[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[N:5][CH:4]=1)#[CH:2].[CH:13]1([C:16]2[CH:17]=[C:18]([NH:30][C:31](=[O:40])[C:32]3[CH:37]=[CH:36][C:35]([CH3:38])=[C:34](I)[CH:33]=3)[CH:19]=[CH:20][C:21]=2[CH2:22][N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)[CH2:15][CH2:14]1>>[N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([C:1]#[C:2][C:36]2[CH:37]=[C:32]([CH:33]=[CH:34][C:35]=2[CH3:38])[C:31]([NH:30][C:18]2[CH:19]=[CH:20][C:21]([CH2:22][N:23]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]3)=[C:16]([CH:13]3[CH2:15][CH2:14]3)[CH:17]=2)=[O:40])=[CH:4][N:5]=1

Participants

Reactant 2

HCID 46839047N-(3-cyclopropyl-4-((4-methylpiperazin-1-yl)methyl)phenyl)-3-iodo-4-methylbenzamide

HCID 577751514-Ethynylcinnoline

Product 1

HCID 577750903-(cinnolin-4-ylethynyl)-N-{3-cyclopropyl-4-[(4-methylpiperazin-1-yl)methyl]phenyl}-4-methylbenzamide

Procedure

The title compound can be synthesized from 4-ethynylcinnoline and N-(3-cyclopropyl-4-((4-methylpiperazin-1-yl)methyl)phenyl)-3-iodo-4-methylbenzamide in a manner similar to that described for Example 1 (nitro reduction performed in a manner similar to that described for Example 10; 0.25M in MeOH/10% AcOH). 4-ethynylcinnoline is prepared from 4-bromocinnoline and ethynyltrimethylsilane according to the 2 steps procedure described in Example 1.

Sources & evidence

ORD record: ord-3573f348fd5349eb9f0dfaea108b2e09
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461167B2

Reaction notes

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