Methanol → HCID 89649146, compound

HRID 2207622Notes

Reaction equation

HRID 2207622 reaction equation
[Br:1][C:2]1[C:7](F)=[CH:6][N:5]=[C:4]([C:9]2[CH2:13][CH2:12][C@:11]3([CH2:17][CH2:16][N:15]([CH3:18])[C:14]3=[O:19])[N:10]=2)[CH:3]=1.[CH3:20][O-:21].[Na+].CO>C1COCC1>[Br:1][C:2]1[C:7]([O:21][CH3:20])=[CH:6][N:5]=[C:4]([C:9]2[CH2:13][CH2:12][C@:11]3([CH2:17][CH2:16][N:15]([CH3:18])[C:14]3=[O:19])[N:10]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 887Methanol3×HCID 10942334Sodium Methoxide3×HCID 89649134HCID 89649134, compound

Product 1

HCID 89649146HCID 89649146, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5R)-2-(4-bromo-5-fluoro-2-pyridyl)-7-methyl-1,7-diazaspiro[4.4]non-1-en-6-one (which may be prepared as described in Description 35) (50 mg, 0.1500 mmol) in THF (2 mL) was added 30% wt. sodium methoxide in methanol (27.6 mg, 0.1500 mmol). The solution was stirred for 10 mins. A further 2 portions of 30% wt. sodium methoxide in methanol (27.6 mg, 0.1500 mmol) were added and the mixture stirred at room temperature for a further 10 mins. A further portion of 30% wt. sodium methoxide in methanol (27.6 mg, 0.1500 mmol) was added and the mixture stirred for 10 mins. The mixture was concentrated and the residues partitioned between water and DCM. The layers were separated with a hydrophobic frit and the organic filtrate evaporated to give (5R)-2-(4-bromo-5-methoxy-2-pyridyl)-7-methyl-1,7-diazaspiro[4.4]non-1-en-6-one (D56) as a cream solid (47 mg);

Workup

  1. stirringthe mixture stirred at room temperature for a further 10 mins
  2. stirringthe mixture stirred for 10 mins
  3. concentrationThe mixture was concentrated
  4. customthe residues partitioned between water and DCM
  5. customThe layers were separated with a hydrophobic frit
  6. customthe organic filtrate evaporated

Sources & evidence

ORD record
ord-74576bb19130458499cd8a5c88097736
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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