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 416285Notes

Reaction equation

HRID 416285 reaction equation
NC1C=CC=CC=1NC(=O)C1C=CC(CNC2N=C(C3C=CC(OCCN(C)C)=CC=3)C=CN=2)=CC=1.NC1C=CC=CC=1NC(C1C=CC2N=C(C3C=CC(OC(F)(F)F)=CC=3)SC=2C=1)=O.C(OC(=O)[NH:73][C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][C:75]=1[NH:80][C:81](=[O:96])[C:82]1[CH:87]=[CH:86][C:85]([CH:88]=[C:89]2[S:93][C:92](=[O:94])[NH:91][C:90]2=[O:95])=[CH:84][CH:83]=1)(C)(C)C>>[NH2:73][C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][C:75]=1[NH:80][C:81](=[O:96])[C:82]1[CH:83]=[CH:84][C:85]([CH:88]=[C:89]2[S:93][C:92](=[O:94])[NH:91][C:90]2=[O:95])=[CH:86][CH:87]=1

Participants

4

Reactant 3

HCID 44570974N-(2-aminophenyl)-4-((4-(4-(2-(dimethylamino)ethoxy)phenyl)pyrimidin-2-ylamino)methyl)benzamideHCID 666221852-(4-Trifluoromethoxy-phenyl)-benzothiazole-6-carboxylic acid (2-aminophenyl)-amideHCID 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-61aacd5e8ad9468aa879aae3a33f2b1d
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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