Aniline → 4-(Benzylamino)-6-(phenylamino)pyridine-3-carboxyamide

HRID 2035483Notes

Reaction equation

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

Participants

Conditions

Temperature: 180 °C

Procedure

To 25 mg of 4-(benzylamino)-6-chloropyridine-3-carboxyamide suspended in 0.2 mL of diphenylether, 18 mg of aniline and 9 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 aqueous sodium bicarbonate, and dried on anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (chloroform:methanol=40:1-10:1) to obtain 30 mg (99%) of the title compound as a slight yellow crystalline powder.

Workup

temperatureAfter cooling
washwashed with saturated aqueous sodium bicarbonate
dry with materialdried on anhydrous sodium sulfate
customThe solvent was evaporated
customthe residue was purified by silica gel column chromatography (chloroform:methanol=40:1-10:1)

Sources & evidence

ORD record: ord-6aa3dddddf274305bec1a3c073ea61a8
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575153B2

Reaction notes

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