Nitrogen → HCID 53819571, compound

HRID 1599480Notes

Reaction equation

HRID 1599480 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][NH:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][C:4](=[O:21])[CH2:3]2.N#N.[H-].[Na+].[CH3:26]I.[NH4+].[Cl-]>CN(C=O)C.O.C(Cl)Cl>[CH3:26][N:9]1[C:10]2[C@:15]([CH3:16])([CH2:14][CH2:13][C:12](=[O:20])[CH:11]=2)[C@@H:17]2[C@H:7]([C@H:6]3[C@@:2]([CH2:19][CH2:18]2)([CH3:1])[CH2:3][C:4](=[O:21])[CH2:5]3)[CH2:8]1

Participants

9

Reactant 5

HCID 947NitrogenHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67628062HCID 67628062, compound

Product 1

HCID 53819571HCID 53819571, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-azaandrost-4-ene-3,16-dione (12, R2 =H) (558 mg, 1.94 mmoles) in DMF (12 mL) was added, in a N2 atmosphere, sodium hydride (60% in mineral oil) (116 mg, 2.91 mmoles) and the mixture stirred at room temperature for 30 minutes. Methyl iodide (1.8 mL, 19.4 mmoles) was added and stirring continued for 2 hours. Saturated NH4Cl (1 mL) was added followed by methylene chloride and H2O. The organic phase was washed with H2O and brine and dried over MgSO4. Evaporation in vacuo and flash chromatography on silica gel with 4% MeOH/CHCl3 gave (13, R2 =H) as a white solid. NMR (CDCl3): δ 0.97 (s, 3H, 18-Me); 1.32 (s, 3H, 19-Me); 2.86 (s, 3H, N-CH3); 5.25 (s, 1H, 4-H).

Workup

  1. stirringstirring
  2. waitcontinued for 2 hours
  3. washThe organic phase was washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. customEvaporation in vacuo and flash chromatography on silica gel with 4% MeOH/CHCl3
  6. customgave (13, R2 =H) as a white solid

Sources & evidence

ORD record
ord-ae983fe44fc34a99ba7bf45dd192fc98
Source dataset
uspto-grants-1998_04
Patent number
US05741795

Reaction notes

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