4-Chloropyridine-2-carboxamide → 4-(4-Amino-2,6-difluorophenoxy)picolinamide

HRID 1670322Notes

Reaction equation

HRID 1670322 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH2:10])=[O:9])[CH:3]=1.FC(F)(F)C(O)=O.NC1C(C2C=CC(CC(N)=O)=CC=2)=C(OC2C=CC(NC(NC(=O)CC3C=CC(F)=CC=3)=O)=CC=2F)C=CN=1.[NH2:57][C:58]1[CH:63]=[C:62]([F:64])[C:61]([OH:65])=[C:60]([F:66])[CH:59]=1>>[NH2:57][C:58]1[CH:63]=[C:62]([F:64])[C:61]([O:65][C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH2:10])=[O:9])[CH:3]=2)=[C:60]([F:66])[CH:59]=1

Participants

4

Reactant 3

HCID 3035434-Chloropyridine-2-carboxamideHCID 27787644-Amino-2,6-difluorophenolHCID 251957421-(4-(2-Amino-3-(4-(2-amino-2-oxoethyl)phenyl)pyridin-4-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)urea trifluoroacetic acid salt

Product 1

HCID 598528534-(4-Amino-2,6-difluorophenoxy)picolinamideYield 29%

Procedure

4-Chloropicolinamide (0.47 g, 3.0 mmol) was converted to the title compound (0.23 g, 29%) in a manner similar to the preparation of Compound C of Example 112, except that 4-amino-2,6-difluorophenol (0.44 g, 3.0 mmol) was used instead of 4-amino-2,5-difluorophenol. 1H NMR (DMSO-d6) δ 8.60 (d, 1H, J=5.6 Hz), 8.22 (br s, 1H), 7.83 (br s, 1H), 7.45-7.46 (m, 1H), 7.30-7.32 (m, 1H), 6.43-6.49 (m, 2H), 5.94 (s, 2H); MS (ESI+) m/z 266 (M+H)+.

Sources & evidence

ORD record
ord-9d2e8c35f1c9462b89952dee76b83dcc
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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