2-Fluoro-N-(2-morpholino-1-phenylethyl)nicotinamide → 2-(4-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-N-(4-fluorobenzyl)nicotinamide, hydrochloride salt

HRID 1986085Notes

Reaction equation

HRID 1986085 reaction equation
[F:1]C1N=CC=CC=1C(NC(C1C=CC=CC=1)CN1CCOCC1)=O.[ClH:25].Cl.[NH:27]1[C:31]2=[N:32][CH:33]=[CH:34][C:35]([O:36][C:37]3[CH:42]=[CH:41][C:40]([NH:43][C:44]4[N:59]=[CH:58][CH:57]=[CH:56][C:45]=4[C:46]([NH:48][C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=4[CH3:55])=[O:47])=[CH:39][C:38]=3[F:60])=[C:30]2[CH:29]=[CH:28]1>>[ClH:25].[NH:27]1[C:31]2=[N:32][CH:33]=[CH:34][C:35]([O:36][C:37]3[CH:42]=[CH:41][C:40]([NH:43][C:44]4[N:59]=[CH:58][CH:57]=[CH:56][C:45]=4[C:46]([NH:48][CH2:49][C:54]4[CH:53]=[CH:52][C:51]([F:1])=[CH:50][CH:55]=4)=[O:47])=[CH:39][C:38]=3[F:60])=[C:30]2[CH:29]=[CH:28]1

Participants

3

Reactant 2

HCID 577213302-Fluoro-N-(2-morpholino-1-phenylethyl)nicotinamideHCID 1317274832-(4-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-N-o-tolylnicotinamide, dihydrochloride salt

Product 1

HCID 162232162-(4-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-N-(4-fluorobenzyl)nicotinamide, hydrochloride saltYield 13%

Procedure

2-Fluoro-N-(2-morpholino-1-phenylethyl)nicotinamide (0.096 g, 0.29 mmol) was converted to the title compound (0.022 g, 13%) 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 12.53 (s, 1H), 10.93-11.05 (m, 2H), 9.73 (d, 1H, J=7.8 Hz), 8.59 (dd, 1H, J=7.9, 1.3 Hz), 8.35 (dd, 1H, J=4.7, 1.4 Hz), 8.20 (d, 1H, J=6.2 Hz), 8.06-8.15 (m, 1H), 7.45-7.55 (m, 3H), 7.23-7.40 (m, 4H), 6.90-6.99 (m, 1H), 6.60 (d, 1H, J=6.2 Hz), 6.38-6.45 (m, 1H), 5.53-5.64 (m, 1H), 3.10-4.00 (m, 10H); HRMS(ESI+), 553.2363 (M+H)+ calc, 553.2368 (M+H)+ found.

Sources & evidence

ORD record
ord-d97bb2889b5f468080b079d2b3c22145
Source dataset
uspto-grants-2009_06
Patent number
US07547782B2

Reaction notes

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