Dimethyl Sulfoxide → N-(4-phenoxy-phenyl)-3-{3-[4-(3,4,5-trimethoxy-phenylamino)-[1,3,5]triazin-2-yl]-pyridin-2-ylamino}benzamide

HRID 983449Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]2[N:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:27][C:28]1[CH:29]=[C:30]([CH:47]=[CH:48][CH:49]=1)[C:31]([NH:33][C:34]1[CH:39]=[CH:38][C:37]([O:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:36][CH:35]=1)=[O:32].CS(C)=O>CO>[O:40]([C:37]1[CH:36]=[CH:35][C:34]([NH:33][C:31](=[O:32])[C:30]2[CH:47]=[CH:48][CH:49]=[C:28]([NH:27][C:2]3[C:7]([C:8]4[N:9]=[C:10]([NH:14][C:15]5[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=5)[N:11]=[CH:12][N:13]=4)=[CH:6][CH:5]=[CH:4][N:3]=3)[CH:29]=2)=[CH:39][CH:38]=1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To [4-(2-chloro-pyridin-3-yl)-[1,3,5]triazin-2-yl]-(3,4,5-trimethoxy-phenyl)amine (Example 2, Step 4)(103 mg, 0.275 mmol) was added 3-amino-N-(4-phenoxyphenyl)-benzamide (297 mg, 0.975 mmol) and DMSO (150 ml), and the mixture was heated overnight at 90° C. The residue was treated with IpOH and MeOH, triturated, sonicated, and filtered to obtain N-(4-phenoxy-phenyl)-3-{3-[4-(3,4,5-trimethoxy-phenylamino)-[1,3,5]triazin-2-yl]-pyridin-2-ylamino}benzamide as a yellow solid: MS m/z 642.5=[M+H]+. Calc'd for C36H31N7O5: 641.24.

Workup

customtriturated
customsonicated
filtrationfiltered

Sources & evidence

ORD record: ord-50d5a71d1e974402878dac29707b08fc
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06864255B2

Reaction notes

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