m-Tolyl isocyanate → HCID 20097077, compound

HRID 1769712Notes

Reaction equation

HRID 1769712 reaction equation
[NH2:1][CH2:2][C:3]([N:5]([CH2:12][C:13]([N:15]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[C:19]([F:24])[CH:18]=1)[CH3:16])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[CH3:25][C:26]1[CH:27]=[C:28]([N:32]=[C:33]=[O:34])[CH:29]=[CH:30][CH:31]=1>>[F:24][C:19]1[CH:18]=[C:17]([N:15]([CH3:16])[C:13](=[O:14])[CH2:12][N:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3](=[O:4])[CH2:2][NH:1][C:33]([NH:32][C:28]2[CH:29]=[CH:30][CH:31]=[C:26]([CH3:25])[CH:27]=2)=[O:34])[CH:22]=[CH:21][C:20]=1[F:23]

Participants

3

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 20097126HCID 20097126, compound

Product 1

HCID 20097077HCID 20097077, compoundYield 10.2%

Procedure

The procedure is analogous to that described in Example 1, but 3.8 g of 2-(2-amino-N-phenylacetamido)-N-(3,4-difluorophenyl)-N-methylacetamide and 1.4 g of 3-methylphenyl isocyanate are used as the starting material. The crude product obtained is purified by chromatography on 80 g of silica (0.065-0.200 mm) contained in a column 2.5 cm in diameter [eluent: ethyl acetate/cyclohexane (75-25 by volume)], collecting 20 cm3 fractions. Fractions 3 to 8 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization from a cyclohexane/ethyl acetate mixture (50-50 by volume), 0.5 g of N-(3,4-difluorophenyl)-N-methyl-2-{2-[3-(3-methylphenyl)ureido]-N-phenylacetamido}acetamide melting at 163° C is obtained.

Workup

  1. customThe crude product obtained
  2. customis purified by chromatography on 80 g of silica (0.065-0.200 mm)
  3. customcollecting 20 cm3 fractions
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  5. customAfter recrystallization from a cyclohexane/ethyl acetate mixture (50-50 by volume)

Sources & evidence

ORD record
ord-f80a6c250a634c1194e42007a326cfc5
Source dataset
uspto-grants-1995_01
Patent number
US05382590

Reaction notes

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