N-(2-aminophenyl)-4-((4-(4-(2-(dimethylamino)ethoxy)phenyl)pyrimidin-2-ylamino)methyl)benzamide → N-(2-Amino-phenyl)-4-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-benzamide

HRID 852958Notes

Reaction equation

HRID 852958 reaction equation
NC1C=CC=CC=1NC(=O)C1C=CC(CNC2N=C(C3C=CC(OCCN(C)C)=CC=3)C=CN=2)=CC=1.C(OC(=O)[NH:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[NH:50][C:51](=[O:66])[C:52]1[CH:57]=[CH:56][C:55]([CH:58]=[C:59]2[S:63][C:62](=[O:64])[NH:61][C:60]2=[O:65])=[CH:54][CH:53]=1)(C)(C)C>>[NH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[NH:50][C:51](=[O:66])[C:52]1[CH:53]=[CH:54][C:55]([CH:58]=[C:59]2[S:63][C:62](=[O:64])[NH:61][C:60]2=[O:65])=[CH:56][CH:57]=1

Participants

3

Reactant 2

HCID 44570974N-(2-aminophenyl)-4-((4-(4-(2-(dimethylamino)ethoxy)phenyl)pyrimidin-2-ylamino)methyl)benzamideHCID 72466473{2-[4-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-benzoylamino]-phenyl}-carbamic acid tert-butyl ester

Product 1

HCID 72466478N-(2-Amino-phenyl)-4-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-benzamideYield 37%

Procedure

Following the procedure described for the synthesis of compound 117 (scheme 28) but substituting the amide 116 by the amide 348, title compound was obtained in 37% yield. 1H NMR: (400 MHz, DMSO-d6, δ (ppm): 9.72 (s, 1H), 8.06 (d, j=8.2 Hz, 2H), 7.79 (s, 1H), 7.69 (d, J=8.4, 2H), 7.14 (d (dd) J=7.8, 1H), 6.95 (d (dd), J=1.6 Hz, J=9.0, 1H), 6.75 (dd, J=1.2 Hz, J=8.0 Hz, 1H), 6.56 (t (dd), J=7.2 Hz 1H). LRMS: 339.4 (calcd.), 340.4 [MH]+ (found).

Sources & evidence

ORD record
ord-78d0f27e71574fadb86aa22c447bdaf0
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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