Pyridine → HCID 21949107, compound

HRID 2376870Notes

Reaction equation

HRID 2376870 reaction equation
[CH:1]1([NH:6][C:7]([N:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21]([NH2:25])[CH:20]=4)=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.N1C=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl[C:40]([O:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:41].[C:49]([O:52][CH2:53][CH3:54])(=[O:51])C>O1CCCC1.CCCCCC>[CH:1]1([NH:6][C:7]([N:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21]([N:25]([C:49]([O:52][C:53]5[CH:54]=[CH:37][CH:36]=[CH:35][CH:34]=5)=[O:51])[C:40](=[O:41])[O:42][C:43]5[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=5)[CH:20]=4)=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

8

Reactant 5

HCID 1049PyridineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 15891Phenyl chloroformateHCID 219491225-[(2-Amino-4-pyridinyl)oxy]-N-cyclopentyl-1H-indole-1-carboxamide

Product 1

HCID 21949107HCID 21949107, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

N1-Cyclopentyl-5-(2-aminopyridin-4-yloxy)-1H-1-indolecarboxamide (1.55 g, 4.58 mmol) was dissolved in tetrahydrofuran (90 ml); triethylamine (1.43 ml, 10.31 mmol) and pyridine (0.56 ml, 6.88 mmol) were added thereto; and the reaction mixture was stirred. The reaction mixture was cooled with ice; phenyl chloroformate (1.44 ml, 11.45 mmol) was added dropwise; and the reaction mixture was stirred at room temperature for 2.5 hours. The reaction mixture was partitioned between ethyl acetate and water; and the organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia BW-300; hexane:ethyl acetate=1:1, 1:3 in this order) to yield the title compound as a colorless amorphous solid (2.516 g, 4.36 mmol, 95.2%).

Workup

  1. temperatureThe reaction mixture was cooled with ice
  2. stirringand the reaction mixture was stirred at room temperature for 2.5 hours
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. washand the organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (Fuji Silysia BW-300

Sources & evidence

ORD record
ord-c6ca8875d6714434855c6d4644b30849
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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