Iodoethane → HCID 70874168, compound

HRID 2208882Notes

Reaction equation

HRID 2208882 reaction equation
[CH3:1][C:2]1[C:3]([NH:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([O:10]C)=[O:9].[H-].[Na+].I[CH2:22][CH3:23].Cl.O1CCOCC1>CN(C=O)C>[CH2:22]([N:12]([CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)[C:3]1[C:2]([CH3:1])=[C:7]([C:8]([OH:10])=[O:9])[CH:6]=[CH:5][N:4]=1)[CH3:23]

Participants

6

Reactant 4

HCID 6340Iodoethane4×HCID 24758Sodium hydride3×HCID 204431481,4-Dioxane hydrochlorideHCID 70873881HCID 70873881, compound

Product 1

HCID 70874168HCID 70874168, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of methyl 3-methyl-2-[(oxan-4-yl)amino]pyridine-4-carboxylate (67 mg, 0.27 mmol) in dry DMF (1.0 ml), was added to a stirred suspension of sodium hydride (60% dispersion in mineral oil, 16 mg, 0.4 mmol) in DMF (0.3 ml) at 0° C. under nitrogen. The reaction mixture was allowed to warm to room temperature and stirred for 30 minutes. The reaction was then treated with iodoethane (16 μl, 0.20 mmol) and stirred for 30 minutes, and then treated again with iodoethane (16 μl, 0.20 mmol) and stirred for a further 30 minutes. The reaction mixture was added to a suspension of sodium hydride (16 mg, 0.4 mmol) in DMF (0.3 ml) at 0° C. Once addition was complete, the reaction mixture was allowed to reach room temperature and stirred for 1 hour before treating with iodoethane (2×16 μl, 0.40 mmol). The reaction mixture was stirred for a further 30 minutes. Sodium hydride (16 mg, 0.4 mmol) was added to the reaction mixture and the mixture stirred for 45 minutes before treating with iodoethane (2×16 μl, 0.40 mmol) and stirred for 15 minutes before adding under nitrogen to a solution of 4M HCl/dioxane (5.0 ml) with cooling.

Workup

  1. stirringstirred for 30 minutes
  2. stirringstirred for a further 30 minutes
  3. additionOnce addition
  4. customto reach room temperature
  5. stirringstirred for 1 hour
  6. stirringThe reaction mixture was stirred for a further 30 minutes
  7. stirringthe mixture stirred for 45 minutes
  8. stirringstirred for 15 minutes
  9. temperaturewith cooling

Sources & evidence

ORD record
ord-13c24d021bbb4676b3983bdf7452d50f
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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