Triethylamine → 2-acetylamino-4-{6-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]pyridin-3-yl}-1H-pyrrole-3-carboxamide

HRID 734641Notes

Reaction equation

HRID 734641 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N:12]=[C:13]=[O:14].[C:15]([NH:18][C:19]1[NH:20][CH:21]=[C:22]([C:27]2[CH:28]=[N:29][C:30]([NH2:33])=[CH:31][CH:32]=2)[C:23]=1[C:24]([NH2:26])=[O:25])(=[O:17])[CH3:16].C(N(CC)CC)C>O1CCCC1>[C:15]([NH:18][C:19]1[NH:20][CH:21]=[C:22]([C:27]2[CH:28]=[N:29][C:30]([NH:33][C:13]([NH:12][C:3]3[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=3[F:1])=[O:14])=[CH:31][CH:32]=2)[C:23]=1[C:24]([NH2:26])=[O:25])(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 578455742-acetylamino-4-(6-aminopyridin-3-yl)-1H-pyrrole-3-carboxamide

Product 1

HCID 578455452-acetylamino-4-{6-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]pyridin-3-yl}-1H-pyrrole-3-carboxamideYield 6.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.068 cm3 (0.466 mmol) of 2-fluoro-5-trifluoromethylphenyl isocyanate is added at a temperature in the region of 23° C. and under an argon atmosphere to 0.11 g (0.424 mmol) of 2-acetylamino-4-(6-aminopyridin-3-yl)-1H-pyrrole-3-carboxamide in solution in 20 cm3 of tetrahydrofuran. After stirring for 1 hour at a temperature in the region of 20° C., 0.059 cm3 (0.424 mmol) of triethylamine is added to the medium. The reaction mixture is then stirred for 18 hours at this temperature and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is purified by flash chromatography [eluent: dichloromethane/methanol (95/5 by volume) and pure ethyl acetate gradient]. After concentrating the fractions under reduced pressure, 0.013 g of 2-acetylamino-4-{6-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]pyridin-3-yl}-1H-pyrrole-3-carboxamide is obtained in the form of a white solid. ES+: m/z=466 (MH+).

Workup

  1. additionis added to the medium
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  3. customThe residue is purified by flash chromatography [eluent: dichloromethane/methanol (95/5 by volume) and pure ethyl acetate gradient]
  4. concentrationAfter concentrating the fractions under reduced pressure

Sources & evidence

ORD record
ord-2a6b8bf08d964e5c874dabe11945767d
Source dataset
uspto-grants-2009_09
Patent number
US07592365B2

Reaction notes

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