Ammonia → 3-Fluoro-5-[(2-fluoro-4-iodophenyl)amino]isonicotinamide

HRID 2167220Notes

Reaction equation

[F:1][C:2]1[CH:10]=[N:9][CH:8]=[C:7]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([I:18])=[CH:14][C:13]=2[F:19])[C:3]=1[C:4](O)=[O:5].C(N1C=CN=C1)([N:22]1C=CN=C1)=O.N>CN(C=O)C>[F:1][C:2]1[CH:10]=[N:9][CH:8]=[C:7]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([I:18])=[CH:14][C:13]=2[F:19])[C:3]=1[C:4]([NH2:22])=[O:5]

Participants

Conditions

Temperature: 60 °C

Procedure

5.000 g of 3-fluoro-5-[(2-fluoro-4-iodophenyl)amino]isonicotinic acid (13.294 mmol, 1. eq.) and 4.980 g of 1,1′-carbonyldiimidazol (30.710 mmol. 2.31 eq) were weighed into a round-bottom flask. 650 mL of dry DMF were added under a nitrogen atmosphere and the resulting mixture was stirred at 60° C. for 1.5 hours. The mixture was cooled to 3° C. in an ice bath, then ammonia (25 weight % in water) was added dropwise and the mixture stirred at room temperature for 18 hours. The resulting slurry was filtered off, the precipitate was rinsed with water and then dried in vacuo to yield 2.54 g (6.36 mmol, 48%) of the analytically pure target compound.

Workup

temperatureThe mixture was cooled to 3° C. in an ice bath
stirringthe mixture stirred at room temperature for 18 hours
filtrationThe resulting slurry was filtered off
washthe precipitate was rinsed with water
customdried in vacuo
customto yield 2.54 g (6.36 mmol, 48%) of the analytically pure target compound

Sources & evidence

ORD record: ord-d579475b8ea44162a77df94373374ed7
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045429B2

Reaction notes

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