2-Isocyanato-1-methoxy-4-methylbenzene → 3-{4-[3-(2-methoxy-5-methylphenyl)ureido]phenyl}-1H-pyrrolo[2,3-c]pyridine-2-carboxamide

HRID 550895

Reaction equation

HRID 550895 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.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=1[N:29]=[C:30]=[O:31]>O1CCCC1.ClCCl>[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=1[NH:29][C:30](=[O:31])[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 41415202-Isocyanato-1-methoxy-4-methylbenzeneHCID 574453513-(4-aminophenyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide

Product 1

HCID 574453183-{4-[3-(2-methoxy-5-methylphenyl)ureido]phenyl}-1H-pyrrolo[2,3-c]pyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 100 mg of 3-(4-aminophenyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide in 5 mL of tetrahydrofuran are added dropwise 54.4 μL of 2-methoxy-5-methylphenyl 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, washed with water and drained by suction. After drying under vacuum, at 40° C., 40 mg of 3-{4-[3-(2-methoxy-5-methylphenyl)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. washwashed with water
  5. customAfter drying under vacuum, at 40° C.

Sources & evidence

ORD record
ord-db5ad32e741b430fb7975fd772da434d
Source dataset
uspto-grants-2011_05
Patent number
US07947706B2

Linked notes

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