N-(3-Fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamide → 2-(2,6-Difluorophenyl)-N-(3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)acetamide

HRID 500838Notes

Reaction equation

HRID 500838 reaction equation
C(N1C2N=CN=C(OC3C=CC(NC(NC(=O)CC4C=CC=CC=4)=S)=CC=3F)C=2C=C1)C1C=CC=CC=1.[F:38][C:39]1[CH:40]=[C:41]([NH:55]C(NC(=O)CC2C=CC=CC=2)=S)[CH:42]=[CH:43][C:44]=1[O:45][C:46]1[CH:51]=[CH:50][N:49]=[C:48]2[CH:52]=[CH:53][S:54][C:47]=12.[F:68][C:69]1[CH:74]=[CH:73][CH:72]=[C:71]([F:75])[C:70]=1[CH2:76][C:77]([N:79]=[C:80]=[S:81])=[O:78]>>[F:68][C:69]1[CH:74]=[CH:73][CH:72]=[C:71]([F:75])[C:70]=1[CH2:76][C:77]([NH:79][C:80](=[S:81])[NH:55][C:41]1[CH:42]=[CH:43][C:44]([O:45][C:46]2[CH:51]=[CH:50][N:49]=[C:48]3[CH:52]=[CH:53][S:54][C:47]=23)=[C:39]([F:38])[CH:40]=1)=[O:78]

Participants

4

Reactant 3

HCID 24901699N-(3-Fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamideHCID 803817992-(2,6-Difluorophenyl)acetyl isothiocyanateHCID 866096601-(4-(7-Benzyl-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-3-fluorophenyl)-3-(2-phenylacetyl)thiourea

Product 1

HCID 866041822-(2,6-Difluorophenyl)-N-(3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)acetamideYield 23%

Procedure

Starting from the amine 169 (scheme 33), following the procedures described above for the synthesis of compound 170a (example 133) but replacing 2-phenylacetyl isothiocyanate with 2-(2,6-difluorophenyl)acetyl isothiocyanate, title compound 192c was obtained in 23% yield. Characterization of 192c is provided in table 18.

Sources & evidence

ORD record
ord-d0a467d6ebc94806af69604654d61c24
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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