2-chloro-N-(2,4-difluorophenyl)nicotinamide → 2-(4-(1h-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)nicotinamide, hydrochloride salt

HRID 1986064Notes

Reaction equation

HRID 1986064 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([O:10][C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=3[F:18])=[C:4]2[CH:3]=[CH:2]1.Cl.N1C2=NC=CC(OC3C=CC(N[C:37]4[C:42]([C:43]([NH:45][C:46]5[CH:51]=[CH:50][C:49]([F:52])=[CH:48][C:47]=5[F:53])=[O:44])=[CH:41][N:40]=[CH:39][CH:38]=4)=CC=3F)=C2C=C1.[Cl:55]C1N=CC=CC=1C(NC1C=CC(F)=CC=1F)=O>>[ClH:55].[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([O:10][C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:41]4[N:40]=[CH:39][CH:38]=[CH:37][C:42]=4[C:43]([NH:45][C:46]4[CH:51]=[CH:50][C:49]([F:52])=[CH:48][C:47]=4[F:53])=[O:44])=[CH:13][C:12]=3[F:18])=[C:4]2[CH:3]=[CH:2]1

Participants

4

Reactant 3

HCID 7367352-chloro-N-(2,4-difluorophenyl)nicotinamideHCID 160379654-((1H-Pyrrolo[2,3-B]pyridin-4-YL)oxy)-3-fluoroaniline2×HCID 162230054-(4-(1h-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)nicotinamide, hydrochloride salt2×

Product 1

HCID 162230072-(4-(1h-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)nicotinamide, hydrochloride saltYield 21%

Procedure

4-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorobenzenamine (0.073 g, 0.30 mmol, Compound C of Example 1) was converted to the title compound (0.032 g, 21%) in a manner similar to the preparation of 4-(4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-N-(2,4-difluorophenyl)nicotinamide hydrochloride salt (Compound D of Example 1), except that 2-chloro-N-(2,4-difluorophenyl)nicotinamide (Maybridge, 0.081 g, 0.30 mmol) was used instead of 4-chloro-N-(2,4-difluorophenyl)nicotinamide. 1H NMR (DMSO-d6) δ 12.83 (s, 1H), 10.75 (s, 1H), 10.52 (s, 1H), 8.28-8.41 (m, 3H), 8.15 (dd, 1H, J=13.6, 2.2 Hz), 7.32-7.56 (m, 5H), 7.09-7.13 (m, 1H), 6.98-7.01 (m, 1H), 6.72 (d, 1H, J=6.5 Hz), 6.48-6.49 (m, 1H); HRMS(ESI+), 476.1334 (M+H)+ calc, 476.1350 (M+H)+ found.

Sources & evidence

ORD record
ord-98ace40e05554b1db20d563c61f84ad7
Source dataset
uspto-grants-2009_06
Patent number
US07547782B2

Reaction notes

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