2-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)nicotinamide, hydrochloride salt → 4-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-2-cyano-n-(2,4-difluorophenyl)pyrimidine-5-carboxamide, dihydrochloride salt
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]([C:35]#[N:36])[N:19]=3)=[CH:13][C:12]=2[F:37])[CH:7]=[CH:6][N:5]=1)(=O)N.[ClH:38].[NH2:39]C1C=C(OC2C=CC(NC3N=CC=CC=3C(NC3C=CC(F)=CC=3F)=O)=CC=2F)C=CN=1>>[ClH:38].[ClH:38].[NH2:39][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]([C:35]#[N:36])[N:19]=3)=[CH:13][C:12]=2[F:37])[CH:7]=[CH:6][N:5]=1Participants
3
Reactant 2
Product 1
Procedure
4-(4-(2-Carbamoylpyridin-4-yloxy)-3-fluorophenylamino)-2-cyano-N-(2,4-difluorophenyl)pyrimidine-5-carboxamide (171 mg, 0.33 mmol) was converted to the title compound (90 mg, 53%) 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 10.85 (s, 1H), 10.83 (s, 1H), 9.11 (s, 1H), 7.99 (m, 2H), 7.83 (br s, 2H), 7.68-7.40 (m, 4H), 7.20 (m, 1H), 6.75 (dd, 1H, J=7.3, 2.4 Hz), 6.20 (d, 1H, J=2.4 Hz); MS(ESI+) m/z 478 (M+H)+.
Sources & evidence
- ORD record
- ord-97cc394936f5490bb73b7e0faea8e82b
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07547782B2
Reaction notes
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