2-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)nicotinamide, hydrochloride salt → 4-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)-2-morpholinopyrimidine-5-carboxamide, trihydrochloride salt

HRID 1986111Notes

Reaction equation

HRID 1986111 reaction equation
C([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]3[C:23]([C:24]([NH:26][C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=4[F:34])=[O:25])=[CH:22][N:21]=[C:20]([N:35]4[CH2:40][CH2:39][O:38][CH2:37][CH2:36]4)[N:19]=3)=[CH:13][C:12]=2[F:41])[CH:7]=[CH:6][N:5]=1)(=O)N.[ClH:42].[NH2:43]C1C=C(OC2C=CC(NC3N=CC=CC=3C(NC3C=CC(F)=CC=3F)=O)=CC=2F)C=CN=1>>[ClH:42].[ClH:42].[ClH:42].[NH2:43][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]3[C:23]([C:24]([NH:26][C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=4[F:34])=[O:25])=[CH:22][N:21]=[C:20]([N:35]4[CH2:40][CH2:39][O:38][CH2:37][CH2:36]4)[N:19]=3)=[CH:13][C:12]=2[F:41])[CH:7]=[CH:6][N:5]=1

Participants

3

Reactant 2

HCID 162231052-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)nicotinamide, hydrochloride saltHCID 577213694-(4-(2-Carbamoylpyridin-4-yloxy)-3-fluorophenylamino)-N-(2,4-difluorophenyl)-2-morpholinopyrimidine-5-carboxamide

Product 1

HCID 1317274954-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)-2-morpholinopyrimidine-5-carboxamide, trihydrochloride saltYield 26%

Procedure

4-(4-(2-Carbamoylpyridin-4-yloxy)-3-fluorophenylamino)-N-(2,4-difluorophenyl)-2-morpholinopyrimidine-5-carboxamide (55 mg, 0.01 mmol) was converted to the title compound (16 mg, 26%) 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 11.24 (s, 1H), 10.20 (s, 1H), 8.85 (s, 1H), 7.92 (m, 2H), 7.82 (br s, 2H), 7.48-7.35 (m, 4H), 7.08 (m, 1H), 6.65 (dd, 1H, J=7.3, 2.5 Hz), 6.12 (d, 1H, J=2.4 Hz), 3.74 (m, 4H) 3.63 (m, 4H); MS(ESI+) m/z 538 (M+H)+.

Sources & evidence

ORD record
ord-fffe8c9513164b4b861fae7e7305b4b7
Source dataset
uspto-grants-2009_06
Patent number
US07547782B2

Reaction notes

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