HCID 11720271, compound → 7-amino-3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-1H-indole-2-carboxamide

HRID 230568Notes

Reaction equation

HRID 230568 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[NH:12][C:13](=[O:36])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:29]3[C:24](=[C:25]([N+:30]([O-])=O)[CH:26]=[CH:27][CH:28]=3)[NH:23][C:22]=2[C:33]([NH2:35])=[O:34])=[CH:17][CH:16]=1>CO.[Pd]>[NH2:30][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:24]=1[NH:23][C:22]([C:33]([NH2:35])=[O:34])=[C:21]2[C:18]1[CH:17]=[CH:16][C:15]([NH:14][C:13]([NH:12][C:3]2[CH:4]=[C:5]([C:8]([F:11])([F:9])[F:10])[CH:6]=[CH:7][C:2]=2[F:1])=[O:36])=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 11720271HCID 11720271, compound

Product 1

HCID 115037557-amino-3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-1H-indole-2-carboxamideYield 40.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3.28 g of palladium-on-charcoal are added to a suspension of 3.42 g (6.82 mmol) of 3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-7-nitro-1H-indole-2-carboxamide in 480 ml of methanol. The reaction mixture is hydrogenated at 30° C. under 3 bar for 2 h in an autoclave, and is then filtered over yridi. The filtrate is evaporated to dryness under reduced pressure. The residue obtained is triturated with ethyl acetate and a small amount of methylene chloride and then filtered. 1.30 g of 7-amino-3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-1H-indole-2-carboxamide are obtained in the form of a gray solid.

Workup

  1. filtrationis then filtered over yridi
  2. customThe filtrate is evaporated to dryness under reduced pressure
  3. customThe residue obtained
  4. customis triturated with ethyl acetate
  5. filtrationa small amount of methylene chloride and then filtered

Sources & evidence

ORD record
ord-b57cad744cff45d3af391abefce03de6
Source dataset
uspto-grants-2009_07
Patent number
US07566736B2

Reaction notes

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