Acetyl chloride → HCID 57756876, compound

HRID 227673Notes

Reaction equation

HRID 227673 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:34])[CH3:33].C(N(CC)CC)C>O1CCCC1.CN(C)C1C=CN=CC=1.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:34])[CH3:33]

Participants

7

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67213118HCID 67213118, compound

Product 1

HCID 57756876HCID 57756876, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To 0.15 g (0.328 mmol) of 4-amino-3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)-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, 0.023 cm3 of acetyl chloride, 0.091 cm3 of triethylamine and 8 mg of 4-dimethylaminopyridine. After stirring for 16 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 to dryness under reduced pressure (2.7 kPa) to give a solid, which is recrystallized while hot from 5 cm3 of dichloromethane. The recrystallized solid is filtered off through a No 3 sinter funnel, washed with twice 3 cm3 of dichloromethane and then dried under reduced pressure (2.7 kPa) at a temperature in the region of 40° C. for 5 hours to give 0.084 g of 4-acetylamino-3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-1H-pyrrole-2-carboxamide in the form of a white solid melting at 228.5° C.; ES+: m/z=464: [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 to dryness under reduced pressure (2.7 kPa)
  6. customto give a solid, which
  7. customis recrystallized while hot from 5 cm3 of dichloromethane
  8. filtrationThe recrystallized solid is filtered off through a No 3 sinter funnel
  9. washwashed with twice 3 cm3 of dichloromethane
  10. customdried under reduced pressure (2.7 kPa) at a temperature in the region of 40° C. for 5 hours

Sources & evidence

ORD record
ord-682097ff911c4bde96babc3c7639dbc1
Source dataset
uspto-grants-2009_07
Patent number
US07560571B2

Reaction notes

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