Triethylamine; trifluoroacetic acid → N-(3-(1-methylethyl)phenyl)-3-((3-(4-pyrimidinyl)-2-pyridinyl)amino)benzamide

HRID 446305Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1C)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([CH3:16])[CH3:15])[CH:9]=1)=[O:6].Cl[C:22]1[C:27]([C:28]2[CH:33]=[CH:32][N:31]=[CH:30][N:29]=2)=[CH:26][CH:25]=[CH:24][N:23]=1.N(CC)(CC)CC.FC(C(O)=O)(F)F>CS(C)=O>[CH3:16][CH:14]([C:10]1[CH:9]=[C:8]([NH:7][C:5](=[O:6])[C:4]2[CH:17]=[CH:18][CH:19]=[C:2]([NH:1][C:22]3[C:27]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][N:29]=4)=[CH:26][CH:25]=[CH:24][N:23]=3)[CH:3]=2)[CH:13]=[CH:12][CH:11]=1)[CH3:15]

Participants

Conditions

Temperature: 90 °C

Procedure

To 3-amino-N-(3-isopropyl-phenyl)-4-methyl-benzamide (300 mg, 1.2 mmol), 4-(2-chloropyridin-3-yl)pyrimidine (100 mg, 0.52 mmol) and DMSO (0.15 mL) was added NEt3-TFA (0.11 mL). The resulting slurry was stirred for 22 hours at 90° C. The crude material was purified by silica gel chromatography (40-60% EtOAc/hexanes) to yield the title compound as a yellow solid. MS m/z=410 [M+1]+. Calc'd for C25H23N5O: 409.49.

Workup

customThe crude material was purified by silica gel chromatography (40-60% EtOAc/hexanes)

Sources & evidence

ORD record: ord-a302deb3c3b3488d94c9fd4ed0a70316
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476434B2

Reaction notes

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