N-(4-(2-(1-Methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamide → 4-(2-(Methylsulfinyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine

HRID 1711070Notes

Reaction equation

HRID 1711070 reaction equation
ClC1C=CN=C2C=C(C3N(C)C=CN=3)[S:10][C:3]=12.CN1C=CN=C1C1SC2C(=NC=CC=2[O:32]C2C=CC(NC(NC(=O)CC3C=CC=CC=3)=S)=CC=2)C=1.Cl.Cl.[F:54][C:55]1[CH:56]=[C:57]([NH:77]C(NC(=O)CC2C=CC=CC=2F)=S)[CH:58]=[CH:59][C:60]=1[O:61][C:62]1[CH:67]=[CH:66][N:65]=[C:64]2[CH:68]=[C:69](C3N(C)C=CN=3)[S:70][C:63]=12>>[CH3:3][S:10]([C:69]1[S:70][C:63]2[C:64](=[N:65][CH:66]=[CH:67][C:62]=2[O:61][C:60]2[CH:59]=[CH:58][C:57]([NH2:77])=[CH:56][C:55]=2[F:54])[CH:68]=1)=[O:32]

Participants

4

Reactant 3

HCID 11962454N-(4-(2-(1-Methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamideHCID 221435637-chloro-2-(1-methyl-1H-imidazol-2-yl)-thieno[3,2-b]pyridineHCID 86604196N-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl carbamothioyl)-2-(2-fluorophenyl)acetamide di-hydrochloride

Product 1

HCID 594245284-(2-(Methylsulfinyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamineYield 31%

Procedure

Starting from the compound 214 (scheme 46) and following the procedures described above for the synthesis of compound 228 (example 202) and 303a (example 232), title compound 234 was obtained in 31% yield as an off-white solid. 1H NMR (d-DMSO) δ (ppm): 12.34 (s, 1H), 11.81 (s, 1H), 8.68 (m, 1H), 8.24 (s, 1H), 7.79 (m, 3H), 7.62 (s, 1H), 7.40-7.13 (m, 6H), 6.86(d, 1H), 4.02 (s, 3H), 3.93 (s, 2H). MS (m/z): 518.1 (M+H) (found).

Sources & evidence

ORD record
ord-e246458f5f7d43708a8491fa2cb5cceb
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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