Phenylacetyl isothiocyanate → Methyl 7-(2-fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)thieno[3,2-b]pyridine-2-carboxylate hydrochloride

Participants

Role	Name	HCID	Charge
Reactant	Phenylacetyl isothiocyanate	HCID 12454157	—
Reactant	Methyl 7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridine-2-carboxylate	HCID 59424438	—
Reactant	N-(4-(1H-Pyrrolo[3,2-b]pyridin-7-yloxy)-3-fluorophenylcarbamothioyl)-2-(2,6-dichlorophenyl)acetamide dihydrochloride	HCID 86604194	—
Product	Methyl 7-(2-fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)thieno[3,2-b]pyridine-2-carboxylate hydrochloride	HCID 86604195	72%

Reaction Steps

Starting from the amine 287, following the procedure described above for the synthesis of compound 269b (scheme 561, example 222) and replacing 2-(2,6-dichlorophenyl)acetyl isothiocyanate with 2-phenylacetyl isothiocyanate, title compound 288 was obtained in 72% yield as a yellowish solid. 1H NMR (d-DMSO) δ (ppm): 12.51(s, 1H), 11.84(s, 1H), 8.64(dd, 1H, J1=5.1 Hz, J2=0.4 Hz), 8.24(s, 1H, J=0.4 Hz), 8.02(dd, 1H, J1=1.8 Hz, J2=13.4 Hz), 7.56-7.54(m, 2H), 7.36-7.31(m, 1H), 7.28-7.25(m, 1H), 6.81 (d, 1H, J=5.5 Hz), 3.91 (s, 3H), 3.81 (s, 2H). MS (m/z):496.3 (M+H) (found).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07772247B2
Source dataset	uspto-grants-2010_08
ORD ID	ord-025ccd5a63da4ec28238116f3ab8c216
Source note	uspto-grants-2010_08