4-(4-(1h-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)nicotinamide, hydrochloride salt → 4-(4-(3-(2,4-Difluorophenylcarbamoyl)pyridin-4-ylamino)-2-fluorophenoxy)picolinamide

HRID 1986071Notes

Reaction equation

Cl.NC1C=C(OC2C=CC(NC3N=CC=CC=3[C:19]([NH:21]C3C=CC(F)=CC=3F)=[O:20])=CC=2F)C=CN=1.Cl.N1[C:40]2=[N:41][CH:42]=[CH:43][C:44]([O:45][C:46]3[CH:51]=[CH:50][C:49]([NH:52][C:53]4[C:58]([C:59]([NH:61][C:62]5[CH:67]=[CH:66][C:65]([F:68])=[CH:64][C:63]=5[F:69])=[O:60])=[CH:57][N:56]=[CH:55][CH:54]=4)=[CH:48][C:47]=3[F:70])=[C:39]2C=C1>>[F:69][C:63]1[CH:64]=[C:65]([F:68])[CH:66]=[CH:67][C:62]=1[NH:61][C:59]([C:58]1[CH:57]=[N:56][CH:55]=[CH:54][C:53]=1[NH:52][C:49]1[CH:50]=[CH:51][C:46]([O:45][C:44]2[CH:43]=[CH:42][N:41]=[C:40]([C:19]([NH2:21])=[O:20])[CH:39]=2)=[C:47]([F:70])[CH:48]=1)=[O:60]

Participants

Reactant 2

HCID 162230054-(4-(1h-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)nicotinamide, hydrochloride salt

HCID 162231052-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)nicotinamide, hydrochloride salt2×

Product 1

HCID 577213614-(4-(3-(2,4-Difluorophenylcarbamoyl)pyridin-4-ylamino)-2-fluorophenoxy)picolinamideYield 12%

Procedure

4-(4-Amino-2-fluorophenoxy)picolinamide (0.12 g, 0.50 mmol, Compound C of Example 3) was converted to the desired compound (0.030 g, 12%) in a manner similar to the preparation of 4-(4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-N-(2,4-di-fluorophenyl)nicotinamide (Step D of Example 1).

Sources & evidence

ORD record: ord-10e5d0ec67b04d2796560c7e32b78add
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547782B2

Reaction notes

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