Triethylamine → HCID 21949267, compound

HRID 2376916Notes

Reaction equation

HRID 2376916 reaction equation
[CH:1]([NH:4][C:5]([N:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH2:23])[CH:18]=3)=[CH:13][CH:14]=2)[CH:9]=[CH:8]1)=[O:6])([CH3:3])[CH3:2].[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27]C)[CH3:25].ClC(OC1C=CC=CC=1)=[O:33].N1CCCC1>O1CCCC1.CN(C)C=O.O>[CH:1]([NH:4][C:5]([N:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:27]([N:26]4[CH2:29][CH2:30][CH2:25][CH2:24]4)=[O:33])[CH:18]=3)=[CH:13][CH:14]=2)[CH:9]=[CH:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 31268PyrrolidineHCID 21949335HCID 21949335, compound

Product 1

HCID 21949267HCID 21949267, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

N1-Isopropyl-5-(2-amino-4-pyridyl)oxy-1H-1-indolecarboxamide (90 mg, 0.29 mmol) was suspended in tetrahydrofuran (2 ml) at room temperature; triethylamine (0.121 mg, 0.868 mmol) and phenyl chloroformate (0.08 ml, 0.633 mmol) was added thereto while stirring; and the reaction mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture; this was subjected to extraction with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. N,N-Dimethylformamide (1 ml) and pyrrolidine (0.2 ml, 2.39 mmol) was added to the residue, and stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water; the organic layer was dried over anhydrous sodium sulfate. This solution was concentrated under reduced pressure; and the residue was purified by silica gel column chromatography (Fuji Silysia NH, ethyl acetate-methanol). The resultant was washed with a solvent mixture (ether:hexane=1:1); and the solid was filtered off to yield the title compound as crystals (65 mg).

Workup

  1. stirringand the reaction mixture was stirred at room temperature for 2 hours
  2. extractionthis was subjected to extraction with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. stirringstirred at room temperature overnight
  7. customThe reaction mixture was partitioned between ethyl acetate and water
  8. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  9. concentrationThis solution was concentrated under reduced pressure
  10. customand the residue was purified by silica gel column chromatography (Fuji Silysia NH, ethyl acetate-methanol)
  11. washThe resultant was washed with a solvent mixture (ether:hexane=1:1)
  12. filtrationand the solid was filtered off

Sources & evidence

ORD record
ord-b0d551a02b714083a64f4229b8c07c5f
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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