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 500900Notes

Reaction equation

HRID 500900 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-39b21f97a5604b2cb513c5f142245464
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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