2-Fluoro-5-(trifluoromethyl)phenyl isocyanate → 3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-1H-pyrrolo[2,3-c]-pyridine-2-carboxamide

HRID 550889

Reaction equation

HRID 550889 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:17]([NH2:19])=[O:18])=[CH:4][CH:3]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=1[N:31]=[C:32]=[O:33]>O1CCCC1.ClCCl>[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=1[NH:31][C:32](=[O:33])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:17]([NH2:19])=[O:18])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 574453513-(4-aminophenyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide

Product 1

HCID 160817373-{4-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-1H-pyrrolo[2,3-c]-pyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 90 mg of 3-(4-aminophenyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide in 5 mL of tetrahydrofuran are added dropwise 50 μL of 2-fluoro-5-(trifluoromethyl)phenyl isocyanate. The reaction mixture is stirred for 16 hours at room temperature under an argon atmosphere and then concentrated under reduced pressure. The residue obtained is stirred for 30 minutes in 2 mL of dichloromethane. The suspended solid is filtered off and drained by suction. After drying under vacuum, at 40° C., 115 mg of 3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-1H-pyrrolo[2,3-c]-pyridine-2-carboxamide are obtained, the characteristics of which are as follows:

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. filtrationThe suspended solid is filtered off
  4. customAfter drying under vacuum, at 40° C.

Sources & evidence

ORD record
ord-60c9fa15c9654d7bad5460c5118e8169
Source dataset
uspto-grants-2011_05
Patent number
US07947706B2

Linked notes

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