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

HRID 500908Notes

Reaction equation

[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[S:15][C:8]=23)=[C:4]([F:22])[CH:3]=1.Cl.Cl.N1C2C(=NC=CC=2OC2C=CC(N[C:42]([NH:44][C:45](=[O:55])[CH2:46][C:47]3[C:52]([Cl:53])=[CH:51][CH:50]=[CH:49][C:48]=3Cl)=[S:43])=CC=2F)C=C1.C1(CC(N=C=S)=O)C=CC=CC=1>>[ClH:53].[F:22][C:4]1[CH:3]=[C:2]([NH:1][C:42]([NH:44][C:45](=[O:55])[CH2:46][C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)=[S:43])[CH:21]=[CH:20][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[CH:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[S:15][C:8]=12

Participants

Reactant 3

HCID 12454157Phenylacetyl isothiocyanate

HCID 59424438Methyl 7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridine-2-carboxylate

HCID 86604194N-(4-(1H-Pyrrolo[3,2-b]pyridin-7-yloxy)-3-fluorophenylcarbamothioyl)-2-(2,6-dichlorophenyl)acetamide dihydrochloride

Product 1

HCID 86604195Methyl 7-(2-fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)thieno[3,2-b]pyridine-2-carboxylate hydrochlorideYield 72%

Procedure

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).

Sources & evidence

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

Reaction notes

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