N-(4-(1H-Pyrrolo[2,3-c]pyridin-7-yloxy)-3-fluorophenylcarbamothioyl)-2-phenylacetamide → N-(4-(6-Bromothieno[3,2-b]pyridin-7-yloxy)-3-fluorophenylcarbamothioyl)-2-phenylacetamide

HRID 1711048Notes

Reaction equation

HRID 1711048 reaction equation
[Br:1][C:2]1[C:3]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]=2[F:19])=[C:4]2[S:10][CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.N1C2=C(OC3C=CC(N[C:37]([NH:39][C:40](=[O:48])[CH2:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)=[S:38])=CC=3F)N=CC=C2C=C1>>[Br:1][C:2]1[C:3]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:37]([NH:39][C:40](=[O:48])[CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[S:38])=[CH:14][C:13]=2[F:19])=[C:4]2[S:10][CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 58621945N-(4-(1H-Pyrrolo[2,3-c]pyridin-7-yloxy)-3-fluorophenylcarbamothioyl)-2-phenylacetamideHCID 594246764-(6-Bromothieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine

Product 1

HCID 59424509N-(4-(6-Bromothieno[3,2-b]pyridin-7-yloxy)-3-fluorophenylcarbamothioyl)-2-phenylacetamideYield 99%

Procedure

Starting from the compound 273 and following the procedure described above for the synthesis of compound 262a (scheme 59, example 218, step 4), title compound 274 was obtained in 99% yield as a white solid. 1H NMR (DMSO-d6) δ (ppm): 12.44 (s, 1H), 11.79(s, 1H), 8.82 (s, 1H), 8.03(d, 1H), 7.99(dd, 1H), 7.54(d, 1H), 7.41(dd, 1H), 7.32-7.24 (m, 6H), 3.80 (s, 2H). MS (m/z): 517.0 (M+H) (found).

Sources & evidence

ORD record
ord-b0bb5146cc0246f7aaab454d27104133
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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