2-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)nicotinamide, hydrochloride salt → 2-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-N-(4-chlorophenyl)-nicotinamide, hydrochloride salt

HRID 1986070Notes

Reaction equation

HRID 1986070 reaction equation
C(C1C=C(OC2C=CC(NC3N=CC=CC=3C(NC3C=CC([Cl:29])=CC=3)=O)=CC=2F)C=CN=1)(=O)N.[ClH:35].[NH2:36][C:37]1[CH:42]=[C:41]([O:43][C:44]2[CH:49]=[CH:48][C:47]([NH:50][C:51]3[N:67]=[CH:66][CH:65]=[CH:64][C:52]=3[C:53]([NH:55][C:56]3[CH:61]=[CH:60][C:59](F)=[CH:58][C:57]=3F)=[O:54])=[CH:46][C:45]=2[F:68])[CH:40]=[CH:39][N:38]=1>>[ClH:29].[NH2:36][C:37]1[CH:42]=[C:41]([O:43][C:44]2[CH:49]=[CH:48][C:47]([NH:50][C:51]3[N:67]=[CH:66][CH:65]=[CH:64][C:52]=3[C:53]([NH:55][C:56]3[CH:61]=[CH:60][C:59]([Cl:35])=[CH:58][CH:57]=3)=[O:54])=[CH:46][C:45]=2[F:68])[CH:40]=[CH:39][N:38]=1

Participants

3

Reactant 2

HCID 162231052-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)nicotinamide, hydrochloride saltHCID 577213502-(4-(2-Carbamoylpyridin-4-yloxy)-3-fluorophenylamino)-N-(4-chlorophenyl)nicotinamide

Product 1

HCID 162231072-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-N-(4-chlorophenyl)-nicotinamide, hydrochloride saltYield 25%

Procedure

2-(4-(2-Carbamoylpyridin-4-yloxy)-3-fluorophenylamino)-N-(4-chlorophenyl)nicotinamide (0.088 g, 0.18 mmol) was converted to the title compound (0.022 g, 25%) in a manner similar to the preparation of 2-(4-(2-aminopyridin-4-yloxy)-3-fluorophenylamino)-N-(2,4-difluorophenyl)nicotinamide (Step E of Example 3). 1H NMR (DMSO-d6) δ 10.65 (s, 1H), 10.40 (s, 1H), 8.36 (dd, 1H, J=4.9, 1.6 Hz), 8.25-8.28 (m, 1H), 8.11 (dd, 1H, J=13.6, 2.4 Hz), 7.71-7.92 (m, 5H), 7.29-7.45 (m, 4H), 6.98 (dd, 1H, J=7.7, 4.9 Hz), 6.65 (dd, 1H, J=7.3, 2.5 Hz), 6.13 (d, 1H, J=2.4 Hz);

Sources & evidence

ORD record
ord-f7b3bc4fa50b4789839e8272b5105f47
Source dataset
uspto-grants-2009_06
Patent number
US07547782B2

Reaction notes

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