Tetrahydrofuran → HCID 16114203, compound

HRID 2070045Notes

Reaction equation

HRID 2070045 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][C:7]=1[C:13]([F:16])([F:15])[F:14].[C:17](N1C=CN=C1)(N1C=CN=C1)=[O:18].C1COCC1.[NH:34]1[C:38]2=[N:39][CH:40]=[CH:41][C:42]([O:43][C:44]3[CH:50]=[CH:49][C:47]([NH2:48])=[CH:46][CH:45]=3)=[C:37]2[CH:36]=[CH:35]1>ClC(Cl)CCl>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:12]=[CH:11][C:9]([NH:10][C:17]([NH:48][C:47]2[CH:49]=[CH:50][C:44]([O:43][C:42]3[CH:41]=[CH:40][N:39]=[C:38]4[NH:34][CH:35]=[CH:36][C:37]=34)=[CH:45][CH:46]=2)=[O:18])=[CH:8][C:7]=1[C:13]([F:14])([F:15])[F:16]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 6485752HCID 6485752, compoundHCID 22936495HCID 22936495, compound

Product 1

HCID 16114203HCID 16114203, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 65741,1,2-TrichloroethaneSolvent

Procedure

4-(2-Methoxyethoxy)-3-(trifluoromethyl)aniline (540 mg, 2.29 mmol) was dissolved in 1,1,2-trichloroethane (5 mL), and carbonyldiimidazole (409 mg) was added thereto under ice-cooling, followed by stirring for 30 minutes. Then, THF (10 mL) and 4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)aniline (517 mg, 2.29 mmol) were added thereto, followed by stirring at room temperature for 20 hours. The reaction solution was partitioned between ethyl acetate (10 mL) and water (20 mL). The organic layer was washed with saturated brine and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (ethyl acetate) to give 1-[4-(2-methoxyethoxy)-3-(trifluoromethyl)phenyl]-3-[4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]urea (880 mg, 79%) as colorless crystals.

Workup

  1. temperatureunder ice-cooling
  2. stirringby stirring at room temperature for 20 hours
  3. customThe reaction solution was partitioned between ethyl acetate (10 mL) and water (20 mL)
  4. washThe organic layer was washed with saturated brine
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica-gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-93631478f1ff419da194247d1356f59d
Source dataset
uspto-grants-2012_10
Patent number
US08299252B2

Reaction notes

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