Methanesulfonic Acid → 4-Cyclohexylamino-6-[(4-morpholinophenyl)amino]pyridine-3-carboxyamide

HRID 2035528Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:11])=[O:10])=[C:4]([NH:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:3]=1.[O:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1.CS(O)(=O)=O>C1(OC2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)Cl>[CH:13]1([NH:12][C:4]2[CH:3]=[C:2]([NH:29][C:28]3[CH:27]=[CH:26][C:25]([N:22]4[CH2:23][CH2:24][O:19][CH2:20][CH2:21]4)=[CH:31][CH:30]=3)[N:7]=[CH:6][C:5]=2[CH2:8][C:9]([NH2:11])=[O:10])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

Conditions

Temperature: 180 °C

Procedure

To 60 mg of 6-chloro-4-(cyclohexylamino)pyridine-3-carboxyamide (the compound of Example 339) suspended in 0.5 mL of diphenyl ether, 84 mg of 4-morpholinoaniline and 23 mg of methanesulfonic acid were added, and stirred at 180° C. for 30 minutes. After cooling, the reaction mixture was dissolved in chloroform, washed with saturated sodium bicarbonate in water, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (chloroform:methanol=40:1 to 20:1) to obtain 77 mg (82%) of the title compound as a light brown crystalline powder.

Workup

temperatureAfter cooling
washwashed with saturated sodium bicarbonate in water
dry with materialdried on anhydrous sodium sulfate
customThe solvent was evaporated
customthe residue was purified by silica gel column chromatography (chloroform:methanol=40:1 to 20:1)

Sources & evidence

ORD record: ord-612b802efcee4792ab5e33a619783ae1
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575153B2

Reaction notes

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