N-(2-Chlorophenyl)-2-fluoronicotinamide → 2-(4-(1h-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-n-(2-chlorophenyl)nicotinamide, dihydrochloride salt

HRID 1986081Notes

Reaction equation

HRID 1986081 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][C:11]=1F.[ClH:18].Cl.[NH:20]1[C:24]2=[N:25][CH:26]=[CH:27][C:28]([O:29][C:30]3[CH:35]=[CH:34][C:33]([NH:36]C4N=CC=CC=4C(NC4C=CC=CC=4C)=O)=[CH:32][C:31]=3[F:53])=[C:23]2[CH:22]=[CH:21]1>>[ClH:1].[ClH:18].[NH:20]1[C:24]2=[N:25][CH:26]=[CH:27][C:28]([O:29][C:30]3[CH:35]=[CH:34][C:33]([NH:36][C:11]4[N:12]=[CH:13][CH:14]=[CH:15][C:10]=4[C:9]([NH:8][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])=[O:17])=[CH:32][C:31]=3[F:53])=[C:23]2[CH:22]=[CH:21]1

Participants

3

Reactant 2

HCID 57721372N-(2-Chlorophenyl)-2-fluoronicotinamideHCID 1317274832-(4-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-N-o-tolylnicotinamide, dihydrochloride salt

Product 1

HCID 1317274852-(4-(1h-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-n-(2-chlorophenyl)nicotinamide, dihydrochloride saltYield 36%

Procedure

N-(2-Chlorophenyl)-2-fluoronicotinamide (0.050 g, 0.20 mmol) was converted to the title compound (0.037 g, 36%) in a manner similar to the preparation of 2-(4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-N-o-tolylnicotinamide (Step B of Example 8). 1H NMR (DMSO-d6) δ 12.75 (s, 1H), 10.80 (s, 1H), 10.49 (s, 1H), 8.10-8.44 (m, 4H), 7.24-7.60 (m, 7H), 6.96-7.10 (m, 1H), 6.70 (m, 1H), 6.45-6.50 (m, 1H); HRMS(ESI+), 474.1133 (M+H)+ calc, 474.1129 (M+H)+ found.

Sources & evidence

ORD record
ord-8b3c73d102ec4be58e9583a32c546cd9
Source dataset
uspto-grants-2009_06
Patent number
US07547782B2

Reaction notes

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