Benzoyl chloride → HCID 57756888, compound

HRID 227674Notes

Reaction equation

HRID 227674 reaction equation
Cl.[NH2:2][C:3]1[C:4]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:22]=3[F:31])=[O:19])=[CH:13][CH:12]=2)=[C:5]([C:8]([NH2:10])=[O:9])[NH:6][CH:7]=1.[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(N(CC)CC)C>O1CCCC1.ClCCl>[C:32]([NH:2][C:3]1[C:4]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:24]=[CH:23][C:22]=3[F:31])=[O:19])=[CH:13][CH:12]=2)=[C:5]([C:8]([NH2:10])=[O:9])[NH:6][CH:7]=1)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 67213118HCID 67213118, compound

Product 1

HCID 57756888HCID 57756888, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To 0.15 g (0.328 mmol) of 4-amino-3-{4-[3-(2-fluoro-5-trifluoromethyl-phenyl)ureido]phenyl}-1H-pyrrole-2-carboxamide hydrochloride dissolved in 4.5 cm3 of tetrahydrofuran are added, at a temperature in the region of 20° C. under an argon atmosphere, 0.038 cm3 of benzoyl chloride and 0.091 cm3 of triethylamine. After stirring for 4 hours at a temperature in the region of 20° C., the reaction mixture is diluted with 15 cm3 of dichloromethane and then washed with twice 10 cm3 of saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure (2.7 kPa) to give a solid, which is recrystallized while hot in 5 cm3 of methanol. The recrystallized solid is filtered through a No 3 sinter funnel, washed with twice 2 cm3 of methanol and then dried under reduced pressure (2.7 kPa) at a temperature in the region of 35° C. for 5 hours to give 0.075 g of 4-benzoylamino-3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)-ureido]phenyl}-1H-pyrrole-2-carboxamide in the form of a white solid melting at 239.7° C.; ES+: m/z=526: [M+H]+.

Workup

  1. additionare added, at a temperature in the region of 20° C. under an argon atmosphere
  2. washwashed with twice 10 cm3 of saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure (2.7 kPa)
  6. customto give a solid, which
  7. customis recrystallized while hot in 5 cm3 of methanol
  8. filtrationThe recrystallized solid is filtered through a No 3 sinter funnel
  9. washwashed with twice 2 cm3 of methanol
  10. customdried under reduced pressure (2.7 kPa) at a temperature in the region of 35° C. for 5 hours

Sources & evidence

ORD record
ord-9ae72f79704646ab96946f7b7612f0cb
Source dataset
uspto-grants-2009_07
Patent number
US07560571B2

Reaction notes

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