N3-Benzyl-2-chloronicotinamide → 4-(4-(3-(Benzylcarbamoyl)pyridin-2-ylamino)-2-fluorophenoxy)picolinamide

HRID 1986072Notes

Reaction equation

HRID 1986072 reaction equation
Cl.N[C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[N:33]=[CH:32][CH:31]=[CH:30][C:18]=3[C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25](F)=[CH:24][C:23]=3F)=[O:20])=[CH:12][C:11]=2[F:34])[CH:6]=[CH:5][N:4]=1.Cl.N1C2=NC=CC(OC3C=CC(NC4C([C:59]([NH:61]C5C=CC(F)=CC=5F)=[O:60])=CN=CC=4)=CC=3F)=C2C=C1.[CH2:71](NC(=O)C1C=CC=NC=1Cl)C1C=CC=CC=1>>[CH2:22]([NH:21][C:19]([C:18]1[C:17]([NH:16][C:13]2[CH:14]=[CH:15][C:10]([O:9][C:7]3[CH:6]=[CH:5][N:4]=[C:3]([C:59]([NH2:61])=[O:60])[CH:8]=3)=[C:11]([F:34])[CH:12]=2)=[N:33][CH:32]=[CH:31][CH:30]=1)=[O:20])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:71]=1

Participants

4

Reactant 3

HCID 2794855N3-Benzyl-2-chloronicotinamideHCID 162230054-(4-(1h-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)nicotinamide, hydrochloride saltHCID 162231052-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)nicotinamide, hydrochloride salt2×

Product 1

HCID 577213414-(4-(3-(Benzylcarbamoyl)pyridin-2-ylamino)-2-fluorophenoxy)picolinamideYield 44%

Procedure

4-(4-Amino-2-fluorophenoxy)picolinamide (0.099 g, 0.40 mmol, Compound C of Example 3) was converted to the desired compound (0.080 g, 44%) in a manner similar to the preparation of 4-(4-(3-(2,4-difluorophenylcarbamoyl)pyridin-4-ylamino)-2-fluorophenoxy)picolinamide (Step D of Example 1), except that N-benzyl-2-chloronicotinamide (Maybridge, 0.099 g, 0.40 mmol) was used instead of 4-chloro-N-(2,4-difluorophenyl)nicotinamide. MS(ESI+) m/z 458 (M+H)+.

Sources & evidence

ORD record
ord-03e0aa2262884e9089a12b42fb70fdcc
Source dataset
uspto-grants-2009_06
Patent number
US07547782B2

Reaction notes

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