Water → 5-[(2-Amino-4-pyridinyl)oxy]-N-cyclopentyl-1H-indole-1-carboxamide

HRID 2376869Notes

Reaction equation

HRID 2376869 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[CH:12]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH:20]1([NH:25][C:26](=O)[O:27]C2C=CC=CC=2)[CH2:24][CH2:23][CH2:22][CH2:21]1.O>CN(C)C=O>[CH:20]1([NH:25][C:26]([N:1]2[C:9]3[C:4](=[CH:5][C:6]([O:10][C:11]4[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[CH:12]=4)=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[O:27])[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 12791466Phenyl cyclopentylcarbamateHCID 219493654-(1H-5-indolyloxy)-2-pyridinamine

Product 1

HCID 219491225-[(2-Amino-4-pyridinyl)oxy]-N-cyclopentyl-1H-indole-1-carboxamideYield 55.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(1H-5-Indolyloxy)-2-pyridinamine (2.50 g, 11.1 mmol, CAS No. 417722-11-3), which was described in WO 02/32872, was dissolved in N,N-dimethylformamide (30 ml); sodium hydride (0.530 g, 13.3 mmol) was added thereto at room temperature; and the reaction mixture was stirred for 30 minutes. Phenyl N-cyclopentylcarbamate (2.50 g, 12.2 mmol) was added thereto at room temperature while stirring; and the reaction mixture was stirred for 30 minutes. Water was added to the reaction mixture; and the precipitated crystals were filtered off, and washed with water. This crystals were dissolved in methanol, and purified by silica gel column chromatography (Fuji Silysia NH; hexane:ethyl acetate=1:1, ethyl acetate, ethyl acetate:methanol=98:2 in this order). The obtained crystals were suspended in hexane: ethanol=10:1, filtered off, washed with hexane, and dried under aeration to yield the title compound as colorless crystals (2.08 g, 6.18 mmol, 55.7%).

Workup

  1. customat room temperature
  2. stirringat room temperature while stirring
  3. stirringand the reaction mixture was stirred for 30 minutes
  4. filtrationand the precipitated crystals were filtered off
  5. washwashed with water
  6. dissolutionThis crystals were dissolved in methanol
  7. custompurified by silica gel column chromatography (Fuji Silysia NH
  8. filtrationethanol=10:1, filtered off
  9. washwashed with hexane
  10. customdried under aeration

Sources & evidence

ORD record
ord-632fa6e5c4a44f77995c572bf4f62275
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

Loading…