2-Chloronicotinonitrile → 3-(3-cyanopyridin-2-ylamino)-N-(3-isopropylphenyl)-4-methylbenzamide

HRID 883033Notes

Reaction equation

Cl[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH2:10][C:11]1[CH:12]=[C:13]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:14]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]([CH3:25])[CH3:24])[CH:18]=1)=[O:15]>C(O)(C(F)(F)F)=O.C(O)(C)C>[C:4]([C:3]1[C:2]([NH:10][C:11]2[CH:12]=[C:13]([CH:26]=[CH:27][C:28]=2[CH3:29])[C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]([CH3:25])[CH3:24])[CH:18]=2)=[O:15])=[N:9][CH:8]=[CH:7][CH:6]=1)#[N:5]

Participants

Conditions

Temperature: 130 °C

Procedure

To 2-chloronicotinonitrile (140 mg, 1.00 mmol) and 3-amino-N-(3-isopropyl-phenyl)-4-methyl-benzamide (80 mg, 0.30 mmol) was added isopropanol (0.8 mL) and TFA (12 drops). The mixture was heated to 130° C. for 16 hours in a sealed tube. The cooled mixture was purified by silica gel chromatography (25% EtOAc/hexanes) to yield 3-(3-cyanopyridin-2-ylamino)-N-(3-isopropylphenyl)-4-methylbenzamide. MS m/z [M+H]+=371; Calc'd for C23H22N4O: 370.46.

Workup

customThe cooled mixture was purified by silica gel chromatography (25% EtOAc/hexanes)

Sources & evidence

ORD record: ord-169618d7afab411a8b4d2a7e500f7760
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236823B2

Reaction notes

Loading…