Sodium ethoxide → HCID 42626124, compound

HRID 1864664Notes

Reaction equation

HRID 1864664 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[C:8]=2[N:14]([CH3:20])[C:15](=O)[O:16]CC)=[CH:4][CH:3]=1.[O-]CC.[Na+].[Na]>C(O)C.O>[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[NH:13][C:15](=[O:16])[N:14]([CH3:20])[C:8]=23)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 42625502Ethyl 4-(4-aminophenoxy)-2-aminopyridin-3-yl-methyl-carbamate

Product 1

HCID 42626124HCID 42626124, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 4-(4-aminophenoxy)-2-aminopyridin-3-yl-methyl-carbamate (180 mg, 0.6 mmol) was suspended in a solution of sodium ethoxide in ethanol, obtained from dissolving sodium (480 mg, 21 mmol) in ethanol (9 ml). The suspension was heated under microwave irradiation for 40 minutes (100° C., 150 W). The mixture was cooled at room temperature, diluted with water and evaporated. The residue was triturated with acetone, and the washings discarded. The solid was dissolved in water and the insoluble solid was filtered off. The filtrate was acidified with HCl 1 M to pH 1, then brought to pH 10 with saturated aqueous Na2CO3. The precipitate formed was recovered by filtration, to afford the title compound (52 mg, 34%). 1H-NMR (δ, ppm, DMSO-d6): 3.49 (s, 3H, CH3N), 5.11 (s, 2H, NH2), 6.29 (d, 1H, HPy,6, J=6.0 Hz), 6.63 (d, 2H, Harom,Ph,3+5, J=8.69 Hz), 6.90 (d, 2H, Harom,Ph,2+6, J=8.73 Hz), 7.74 (d, 1H, HPy,6, J=5.96 Hz), 11.53 (s, 1H, NHPy2). LC-MS (m/z): 257 (M+H, 100).

Workup

  1. customobtained
  2. temperatureThe mixture was cooled at room temperature
  3. customevaporated
  4. customThe residue was triturated with acetone
  5. dissolutionThe solid was dissolved in water
  6. filtrationthe insoluble solid was filtered off
  7. customThe precipitate formed
  8. filtrationwas recovered by filtration

Sources & evidence

ORD record
ord-df1fc43fe78f43adb22105370ff5d90c
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

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