N-(3-cyclopropyl-4-((4-methylpiperazin-1-yl)methyl)phenyl)-3-iodo-4-methylbenzamide → 3-[(2-amino-1,3-thiazol-5-yl)ethynyl]-N-{3-cyclopropyl-4-[(4-methylpiperazin-1-yl)methyl]phenyl}-methylbenzamide

HRID 2059802Notes

Reaction equation

HRID 2059802 reaction equation
[C:1]([C:3]1[S:7][C:6]([NH:8]C(=O)OC(C)(C)C)=[N:5][CH:4]=1)#[CH:2].[CH:16]1([C:19]2[CH:20]=[C:21]([NH:33][C:34](=[O:43])[C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[C:37](I)[CH:36]=3)[CH:22]=[CH:23][C:24]=2[CH2:25][N:26]2[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]2)[CH2:18][CH2:17]1>>[NH2:8][C:6]1[S:7][C:3]([C:1]#[C:2][C:41]2[C:36]([CH3:37])=[C:35]([CH:40]=[CH:39][CH:38]=2)[C:34]([NH:33][C:21]2[CH:22]=[CH:23][C:24]([CH2:25][N:26]3[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH2:31]3)=[C:19]([CH:16]3[CH2:18][CH2:17]3)[CH:20]=2)=[O:43])=[CH:4][N:5]=1

Participants

3

Reactant 2

HCID 46839047N-(3-cyclopropyl-4-((4-methylpiperazin-1-yl)methyl)phenyl)-3-iodo-4-methylbenzamideHCID 57737416Tert-butyl (5-ethynylthiazol-2-yl)carbamate

Product 1

HCID 866311073-[(2-amino-1,3-thiazol-5-yl)ethynyl]-N-{3-cyclopropyl-4-[(4-methylpiperazin-1-yl)methyl]phenyl}-methylbenzamide

Procedure

The title compound can be synthesized from tert-butyl (5-ethynyl-1,3-thiazol-2-yl)carbamate and N-(3-cyclopropyl-4-((4-methylpiperazin-1-yl)methyl)phenyl)-3-iodo-4-methylbenzamide in a manner similar to that described for Example 2 (nitro reduction performed in a manner similar to that described for Example 8; 0.25M in MeOH/10% AcOH). T-BOC deprotection can be performed after coupling as described in Example 5.

Sources & evidence

ORD record
ord-ef855e9658b54252b90c9469c9b718f3
Source dataset
uspto-grants-2012_10
Patent number
US08278307B2

Reaction notes

Loading…