1-Phenylcyclopropanecarbonyl isothiocyanate → N-(3-Fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl) 1-phenylcyclopropanecarboxamide

HRID 500839Notes

Reaction equation

HRID 500839 reaction equation
[CH2:1](N1C2N=CN=C(OC3C=CC(NC(NC(=O)CC4C=CC=CC=4)=S)=CC=3F)C=2C=C1)[C:2]1C=CC=CC=1.[F:38][C:39]1[CH:40]=[C:41]([NH:55][C:56]([NH:58][C:59](=[O:67])[CH2:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)=[S:57])[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.C1(C2(C(N=C=S)=O)CC2)C=CC=CC=1>>[F:38][C:39]1[CH:40]=[C:41]([NH:55][C:56]([NH:58][C:59]([C:60]2([C:61]3[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=3)[CH2:2][CH2:1]2)=[O:67])=[S:57])[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

Participants

4

Reactant 3

HCID 218906101-Phenylcyclopropanecarbonyl isothiocyanateHCID 24901699N-(3-Fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamideHCID 866096601-(4-(7-Benzyl-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-3-fluorophenyl)-3-(2-phenylacetyl)thiourea

Product 1

HCID 86604183N-(3-Fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl) 1-phenylcyclopropanecarboxamideYield 41%

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 1-phenylcyclopropanecarbonyl isothiocyanate, title compound 192d was obtained in 41% yield. Characterization of 192d is provided in table 18.

Sources & evidence

ORD record
ord-d43cd4bddb554b2abe707f2257522a32
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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