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

HRID 1986067Notes

Reaction equation

[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13]([NH2:15])=[O:14])[CH:8]=2)=[C:4]([F:18])[CH:3]=1.Cl.N1C2=NC=CC(OC3C=CC(N[C:37]4[N:53]=[CH:52][CH:51]=[CH:50][C:38]=4[C:39]([NH:41][C:42]4[CH:47]=[CH:46][C:45]([F:48])=[CH:44][C:43]=4[F:49])=[O:40])=CC=3F)=C2C=C1>>[C:13]([C:9]1[CH:8]=[C:7]([O:6][C:5]2[CH:16]=[CH:17][C:2]([NH:1][C:37]3[N:53]=[CH:52][CH:51]=[CH:50][C:38]=3[C:39]([NH:41][C:42]3[CH:47]=[CH:46][C:45]([F:48])=[CH:44][C:43]=3[F:49])=[O:40])=[CH:3][C:4]=2[F:18])[CH:12]=[CH:11][N:10]=1)(=[O:14])[NH2:15]

Participants

Reactant 2

HCID 162230072-(4-(1h-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)nicotinamide, hydrochloride salt

HCID 231532054-(4-Amino-2-fluorophenoxy)picolinamide

Product 1

HCID 577213642-(4-(2-Carbamoylpyridin-4-yloxy)-3-fluorophenylamino)-N-(2,4-difluorophenyl)nicotinamideYield 37%

Procedure

4-(4-Amino-2-fluorophenoxy)picolinamide (0.12 g, 0.50 mmol) was converted to the desired compound (0.088 g, 37%) in a manner similar to the preparation of 2-(4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-N-(2,4-difluorophenyl)-nicotinamide (Example 2). HRMS(ESI+), 480.1283 (M+H)+ calc, 480.1281 (M+H)+ found.

Sources & evidence

ORD record: ord-2b5c3457401646ffba13bbd1a766cb45
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547782B2

Reaction notes

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