Water → HCID 23117207, compound

HRID 900694Notes

Reaction equation

Cl.Cl.Cl.[NH2:4][CH2:5][CH2:6][NH:7][C:8]1[C:34]([Cl:35])=[CH:33][C:11]([C:12]([NH:14][C:15]2[S:16][C:17]([CH2:26][N:27]([CH2:29][CH2:30][CH2:31][CH3:32])[CH3:28])=[C:18]([C:20]3[S:21][CH:22]=[C:23]([Cl:25])[CH:24]=3)[N:19]=2)=[O:13])=[CH:10][N:9]=1.C(N(CC)CC)C.[CH3:43][S:44](Cl)(=[O:46])=[O:45].O>C1COCC1>[CH2:29]([N:27]([CH2:26][C:17]1[S:16][C:15]([NH:14][C:12](=[O:13])[C:11]2[CH:33]=[C:34]([Cl:35])[C:8]([NH:7][CH2:6][CH2:5][NH:4][S:44]([CH3:43])(=[O:46])=[O:45])=[N:9][CH:10]=2)=[N:19][C:18]=1[C:20]1[S:21][CH:22]=[C:23]([Cl:25])[CH:24]=1)[CH3:28])[CH2:30][CH2:31][CH3:32]

Participants

Conditions

Temperature: 0 °C

Procedure

100 mg of 6-[(2-aminoethyl)amino]-N-[5-{[butyl(methyl)amino]methyl}-4-(4-chlorothiophen-2-yl)thiazol-2-yl]-5-chloronicotinamide trihydrochloride was suspended in 5 ml of THF, and 85 μl of triethylamine was added, followed by cooling to 0° C. 13 μl of methanesulfonyl chloride was added to the solution, and the mixture was stirred at room temperature for 2 hours. The reaction solution was poured into water, and extracted with chloroform. The organic layer was washed with water and with brine, and then dried over magnesium sulfate. After the solvent was distilled off, the residue was purified by silica gel column chromatography (chloroform:MeOH =10:1) to obtain 75 mg of N-[5-{[butyl(methyl)amino]methyl}-4-(4-chlorothiophen-2-yl)thiazol-2-yl]-5-chloro-6-({2-[(methylsulfonyl)amino]ethyl}amino)nicotinamide.

Workup

extractionextracted with chloroform
washThe organic layer was washed with water and with brine
dry with materialdried over magnesium sulfate
distillationAfter the solvent was distilled off
customthe residue was purified by silica gel column chromatography (chloroform:MeOH =10:1)

Sources & evidence

ORD record: ord-14ebc9d179c84e7bbb229e79da2304ae
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07361658B2

Reaction notes

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