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

HRID 1986083Notes

Reaction equation

HRID 1986083 reaction equation
F[C:2]1[N:18]=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)=[O:5].[ClH:19].Cl.[NH:21]1[C:25]2=[N:26][CH:27]=[CH:28][C:29]([O:30][C:31]3[CH:36]=[CH:35][C:34]([NH:37]C4N=CC=CC=4C(NC4C=CC=CC=4C)=O)=[CH:33][C:32]=3[F:54])=[C:24]2[CH:23]=[CH:22]1>>[ClH:19].[ClH:19].[NH:21]1[C:25]2=[N:26][CH:27]=[CH:28][C:29]([O:30][C:31]3[CH:36]=[CH:35][C:34]([NH:37][C:2]4[N:18]=[CH:17][CH:16]=[CH:15][C:3]=4[C:4]([NH:6][CH2:7][C:8]4[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=4)=[O:5])=[CH:33][C:32]=3[F:54])=[C:24]2[CH:23]=[CH:22]1

Participants

3

Reactant 2

HCID 577213352-Fluoro-N-(4-fluorobenzyl)nicotinamideHCID 1317274832-(4-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-N-o-tolylnicotinamide, dihydrochloride salt

Product 1

HCID 1317274862-(4-(1h-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-n-(4-fluorobenzyl)nicotinamide, dihydrochloride saltYield 35%

Procedure

2-Fluoro-N-(4-fluorobenzyl)nicotinamide (0.050 g, 0.20 mmol) was converted to the title compound (0.035 g, 35%) 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 12.63 (s, 1H), 11.17 (s, 1H), 9.44 (t, 1H, J=5.8 Hz), 8.10-8.40 (m, 4H), 7.50-7.60 (m, 1H), 7.30-7.45 (m, 4H), 7.08-7.10 (m, 2H), 6.90-6.95 (m, 1H), 6.66 (d, 1H, J=6.3 Hz), 6.43-6.46 (m, 1H), 4.44 (d, 2H, J=5.7 Hz); HRMS(ESI+), 472.1585 (M+H)+ calc, 472.1587 (M+H)+ found.

Sources & evidence

ORD record
ord-0b057009c56141bd97ff35012cafa2e5
Source dataset
uspto-grants-2009_06
Patent number
US07547782B2

Reaction notes

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