2-[2-(4-Methylpiperazin-1-yl)ethoxy]aniline → N-methyl-4-(2-(2-(2-(4-methylpiperazin-1-yl)ethoxy)phenylamino)benzo[d]thiazol-6-yloxy)picolinamide

HRID 2370568

Reaction equation

[CH3:1][NH:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:22]=[CH:21][C:14]3[N:15]=[C:16](S(C)=O)[S:17][C:13]=3[CH:12]=2)[CH:7]=[CH:6][N:5]=1.[CH3:24][N:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][O:33][C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[NH2:36])[CH2:27][CH2:26]1>CC(O)C.Cl>[CH3:1][NH:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:22]=[CH:21][C:14]3[N:15]=[C:16]([NH:36][C:35]4[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=4[O:33][CH2:32][CH2:31][N:28]4[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]4)[S:17][C:13]=3[CH:12]=2)[CH:7]=[CH:6][N:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To the solution of N-methyl-4-(2-(methylsulfinyl)benzo[d]thiazol-6-yloxy)picolinamide (25 mg, 0.072 mmol, 1.0 eq) in 1 mL of IPA and 1 mL conc. HCl was added 2-(2-(4-methylpiperazin-1-yl)ethoxy) aniline (25 mg, 0.108 mmol, 1.5 eq) and reaction mixture heated at 80° C. in oil bath for 2 hours. Thereafter, the product was purified via reverse phase HPLC. This procedure was generalized for other analogues for which progress of the reaction was monitored by LC-MS and amount of aniline and reaction time adjusted as needed. LC/MS (m/z) [519.1] (MH+)

Workup

customThereafter, the product was purified via reverse phase HPLC
customwas monitored by LC-MS and amount of aniline and reaction time

Sources & evidence

ORD record: ord-15936e34814449d49671021b09d6a5d4
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710048B2

Linked notes

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