N3-Benzyl-2-chloronicotinamide → 2-(4-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-N-benzylnicotinamide, dihydrochloride salt

HRID 1986074Notes

Reaction equation

HRID 1986074 reaction equation
[ClH:1].[NH:2]1[C:6]2=[N:7][CH:8]=[CH:9][C:10]([O:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18]C4C(C(NC5C=CC(F)=CC=5F)=O)=CN=CC=4)=[CH:14][C:13]=3[F:36])=[C:5]2[CH:4]=[CH:3]1.[CH2:37]([NH:44][C:45](=[O:53])[C:46]1[CH:51]=[CH:50][CH:49]=[N:48][C:47]=1[Cl:52])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[ClH:52].[ClH:1].[NH:2]1[C:6]2=[N:7][CH:8]=[CH:9][C:10]([O:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:47]4[N:48]=[CH:49][CH:50]=[CH:51][C:46]=4[C:45]([NH:44][CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[O:53])=[CH:14][C:13]=3[F:36])=[C:5]2[CH:4]=[CH:3]1

Participants

3

Reactant 2

HCID 2794855N3-Benzyl-2-chloronicotinamideHCID 162230054-(4-(1h-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)nicotinamide, hydrochloride salt4×

Product 1

HCID 1317274822-(4-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-N-benzylnicotinamide, dihydrochloride saltYield 17%

Procedure

4-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorobenzenamine (0.043 g, 0.18 mmol, Compound C of Example 1) was converted to the title compound (0.015 g, 17%) 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 N-benzyl-2-chloronicotinamide (Maybridge, 0.043 g, 0.18 mmol) was used instead of 4-chloro-N-(2,4-difluorophenyl)nicotinamide.

Sources & evidence

ORD record
ord-67c67e7476584e2c95fb44dca10dc9ed
Source dataset
uspto-grants-2009_06
Patent number
US07547782B2

Reaction notes

Loading…