Chloroform → 6-[(2-Aminophenyl)amino]-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide

HRID 2035537Notes

Reaction equation

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

Participants

Conditions

Temperature: 180 °C

Procedure

To 89 mg of 6-chloro-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide (the compound of Example 20) suspended in 3 mL of diphenylether, 65 mg of 1,2-phenylenediamine and 144 mg of methanesulfonic acid were added, and stirred in a nitrogen atmosphere at 180° C. for 30 minutes. After cooling, chloroform was added to the reaction mixture to dissolve the deposit, washed with saturated sodium bicarbonate, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (chloroform:methanol:ammonia water=10:1:0.1) to obtain 18 mg (yield 17%) of the title compound as a light brown powder.

Workup

temperatureAfter cooling
dissolutionto dissolve the deposit
washwashed with saturated sodium bicarbonate
dry with materialdried on anhydrous sodium sulfate
customThe solvent was evaporated
customthe residue was purified by silica gel column chromatography (chloroform:methanol:ammonia water=10:1:0.1)

Sources & evidence

ORD record: ord-e808c5dd5e1f4b5fafb0ad69e2caba11
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575153B2

Reaction notes

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