2-Fluoro-5-(trifluoromethyl)phenyl isocyanate → HCID 57845560, compound

HRID 734647Notes

Reaction equation

HRID 734647 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].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23]([C:33]([NH2:35])=[O:34])=[C:24]([NH:27][C:28]([NH:30][CH2:31][CH3:32])=[O:29])[NH:25][CH:26]=2)=[CH:18][CH:17]=1>O1CCCC1>[CH2:31]([NH:30][C:28](=[O:29])[NH:27][C:24]1[NH:25][CH:26]=[C:22]([C:19]2[CH:20]=[CH:21][C:16]([NH:15][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:17][CH:18]=2)[C:23]=1[C:33]([NH2:35])=[O:34])[CH3:32]

Participants

4

Reactant 2

HCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 69059862HCID 69059862, compound

Product 1

HCID 57845560HCID 57845560, compoundYield 200.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

0.031 cm3 (0.0213 mmol) of 2-fluoro-5-trifluoromethylphenyl isocyanate is added at a temperature in the region of 25° C. to 0.056 g (0.194 mmol) of 4-(4-aminophenyl)-2-(3-ethylureido)-1H-pyrrole-3-carboxamide in solution in 20 cm3 of tetrahydrofuran. After stirring for 16 hours at a temperature in the region of 60° C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is then diluted in 40 cm3 of ethyl acetate and then washed with twice 30 cm3 of water. The organic solution is dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is purified by flash chromatography [eluent: dichloromethane/methanol/acetonitrile (95/2.5/2.5 by volume)]. After concentrating the fractions under reduced pressure, 0.021 g of 2-(3-ethylureido)-4-{4-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-1H-pyrrole-3-carboxamide is obtained in the form of a yellow solid. ES+: m/z=494 (MH+).

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. additionThe residue is then diluted in 40 cm3 of ethyl acetate
  3. washwashed with twice 30 cm3 of water
  4. dry with materialThe organic solution is dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customto give a residue which
  8. customis purified by flash chromatography [eluent: dichloromethane/methanol/acetonitrile (95/2.5/2.5 by volume)]
  9. concentrationAfter concentrating the fractions under reduced pressure

Sources & evidence

ORD record
ord-3ca06cdf01034fac8dab2a5c44a2b61a
Source dataset
uspto-grants-2009_09
Patent number
US07592365B2

Reaction notes

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