Triethylamine → HCID 21949250, compound

HRID 2376915Notes

Reaction equation

HRID 2376915 reaction equation
[CH2:1]([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])[CH2:2][CH3:3].[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>[CH2:1]([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])[CH2:2][CH3:3]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 31268PyrrolidineHCID 21949354HCID 21949354, compound

Product 1

HCID 21949250HCID 21949250, compoundYield 6.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

N1-Propyl-5-(2-amino-4-pyridyl)oxy-1H-1-indolecarboxamide (477 mg, 1.54 mmol) was suspended in tetrahydrofuran (5 ml) at room temperature; triethylamine (0.536 mg, 3.08 mmol) and phenyl chloroformate (0.389 ml, 3.85 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 (3 ml) and pyrrolidine (0.27 ml, 3.23 mmol) was added to the residue; and the reaction mixture was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water; and the organic layer was dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure; the residue was purified by silica gel column chromatography (Fuji Silysia NH, ethyl acetate-methanol). The resultant was washed with a solvent mixture of ether:hexane=1:1; and the solid was filtered off to yield crystals (40 mg) of the title compound.

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. stirringand the reaction mixture was stirred at room temperature overnight
  7. customThe reaction mixture was partitioned between ethyl acetate and water
  8. dry with materialand the organic layer was dried over anhydrous sodium sulfate
  9. concentrationThe solution was concentrated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (Fuji Silysia NH, ethyl acetate-methanol)
  11. washThe resultant was washed with a solvent mixture of ether
  12. filtrationand the solid was filtered off

Sources & evidence

ORD record
ord-0d5df007a02f4620a49bc6db629cac38
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

Loading…