2-chloro-N-(4-chlorophenyl)pyridine-3-carboxamide → 2-(4-(2-Carbamoylpyridin-4-yloxy)-3-fluorophenylamino)-N-(4-chlorophenyl)nicotinamide

HRID 1986069Notes

Reaction equation

HRID 1986069 reaction equation
Cl.NC1C=C(OC2C=CC(NC3N=CC=CC=3C(NC3C=CC(F)=CC=3F)=O)=CC=2F)C=CN=1.[C:35]([C:38]1[CH:43]=[C:42]([O:44][C:45]2[CH:50]=[CH:49][C:48]([NH:51][C:52]3[N:68]=[CH:67][CH:66]=[CH:65][C:53]=3[C:54]([NH:56][C:57]3[CH:62]=[CH:61][C:60](F)=[CH:59][C:58]=3F)=[O:55])=[CH:47][C:46]=2[F:69])[CH:41]=[CH:40][N:39]=1)(=[O:37])[NH2:36].[Cl:70]C1N=CC=CC=1C(NC1C=CC(Cl)=CC=1)=O>>[C:35]([C:38]1[CH:43]=[C:42]([O:44][C:45]2[CH:50]=[CH:49][C:48]([NH:51][C:52]3[N:68]=[CH:67][CH:66]=[CH:65][C:53]=3[C:54]([NH:56][C:57]3[CH:62]=[CH:61][C:60]([Cl:70])=[CH:59][CH:58]=3)=[O:55])=[CH:47][C:46]=2[F:69])[CH:41]=[CH:40][N:39]=1)(=[O:37])[NH2:36]

Participants

4

Reactant 3

HCID 5879062-chloro-N-(4-chlorophenyl)pyridine-3-carboxamideHCID 162231052-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)nicotinamide, hydrochloride salt2×HCID 577213642-(4-(2-Carbamoylpyridin-4-yloxy)-3-fluorophenylamino)-N-(2,4-difluorophenyl)nicotinamide

Product 1

HCID 577213502-(4-(2-Carbamoylpyridin-4-yloxy)-3-fluorophenylamino)-N-(4-chlorophenyl)nicotinamideYield 47%

Procedure

4-(4-Amino-2-fluorophenoxy)picolinamide (0.12 g, 0.50 mmol, Compound C of Example 3) was converted to the desired compound (0.090 g, 47%) in a manner similar to the preparation of 2-(4-(2-carbamoylpyridin-4-yloxy)-3-fluorophenylamino)-N-(2,4-difluorophenyl)-nicotinamide (Step D of Example 3), except that 2-chloro-N-(4-chlorophenyl)nicotinamide (Maybridge, 0.11 g, 0.40 mmol) was used instead of 2-chloro-N-(2,4-difluorophenyl)nicotinamide. HRMS(ESI+), 478.1082 (M+H)+ calc, 478.1059 (M+H)+ found.

Sources & evidence

ORD record
ord-590ee7320b6a4898b4a5a2071675ec85
Source dataset
uspto-grants-2009_06
Patent number
US07547782B2

Reaction notes

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