Acetic Anhydride → N-{3-[3-(2-Chloro-4,5-difluorobenzoyl)ureido]-4-methoxyphenyl}acetamide

HRID 349731Notes

Reaction equation

HRID 349731 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([F:23])[C:20]([F:24])=[CH:19][C:3]=1[C:4]([NH:6][C:7]([NH:9][C:10]1[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][C:11]=1[O:17][CH3:18])=[O:8])=[O:5].CN1CC[CH2:28][C:27]1=[O:31].C(OC(=O)C)(=O)C>O>[Cl:1][C:2]1[CH:22]=[C:21]([F:23])[C:20]([F:24])=[CH:19][C:3]=1[C:4]([NH:6][C:7](=[O:8])[NH:9][C:10]1[CH:15]=[C:14]([NH:16][C:27](=[O:31])[CH3:28])[CH:13]=[CH:12][C:11]=1[O:17][CH3:18])=[O:5]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 13387N-methyl-2-pyrrolidoneHCID 115665791-(2-Chloro-4,5-difluorobenzoyl)-3-(5-amino-2-methoxyphenyl)urea

Product 1

HCID 9887086N-{3-[3-(2-Chloro-4,5-difluorobenzoyl)ureido]-4-methoxyphenyl}acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.10 g (0.3 mmol) of 1-(2-chloro-4,5-difluorobenzoyl)-3-(5-amino-2-methoxyphenyl)urea was admixed with 1 ml of N-methylpyrrolidone, 0.11 g (0.3 mmol) of acetic anhydride and stirred at room temperature for 2 hours. The mixture was diluted with 20 ml of H2O and extracted three times with 20 ml of ethyl acetate each time. The combined organic phase was washed with H2O, concentrated and dried. The crude product was purified by preparative HPLC (column: Waters Xterra™ MS C18, 5 μm, 30×100 mm, eluent: A: H2O+0.2% trifluoroacetic acid, B: acetonitrile, gradient: 2.5 minutes 90% A/10% B to 17.5 minutes 10% A/90% B). 0.03 g of the desired product was obtained.

Workup

  1. extractionextracted three times with 20 ml of ethyl acetate each time
  2. washThe combined organic phase was washed with H2O
  3. concentrationconcentrated
  4. customdried
  5. customThe crude product was purified by preparative HPLC (column
  6. waitWaters Xterra™ MS C18, 5 μm, 30×100 mm, eluent: A: H2O+0.2% trifluoroacetic acid, B: acetonitrile, gradient: 2.5 minutes 90% A/10% B to 17.5 minutes 10% A/90% B)

Sources & evidence

ORD record
ord-45feb3582698417a8dfc24969f13cb0c
Source dataset
uspto-grants-2007_02
Patent number
US07179941B2

Reaction notes

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