Methanol → HCID 18316018, compound

HRID 276296Notes

Reaction equation

HRID 276296 reaction equation
[CH3:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[CH:5]=[C:4]([N:11]=[C:12]2[S:16][CH2:15][C:14]3([CH2:20][CH2:19][CH2:18][CH2:17]3)[NH:13]2)[N:3]=1.[CH2:21](Br)[CH:22]([CH3:24])[CH3:23].[H-].[Na+].CO>CN(C=O)C>[CH3:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[CH:5]=[C:4]([N:11]=[C:12]2[S:16][CH2:15][C:14]3([CH2:20][CH2:19][CH2:18][CH2:17]3)[N:13]2[CH2:21][CH:22]([CH3:24])[CH3:23])[N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 65551-Bromo-2-methylpropaneHCID 24758Sodium hydrideHCID 178428285HCID 178428285, compound

Product 1

HCID 18316018HCID 18316018, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(2,4-dimethyl-3-cyano-6-pyridylimino)-3-thia-1-azaspiro[4.4]nonane (Method C1e; 0.192 g, 0.669 mmol) and isobutyl bromide (0.5 mL) in anh. DMF (0.5 mL) was added NaH (95%; 0.62 g, 6.69 mmol) portionwise. The resulting mixture was heated at 50° C. for 3 h, then treated with MeOH (approximately 0.5 mL) and concentrated under reduced pressure. The residue was purified by chromatography (SiO2, gradient from 20% EtOAc/hex to 100% CH2Cl2) to give 2-(2,4-dimethyl-3-cyano-6-pyridylimino)-1-isobutyl-3-thia-1-azaspiro[4.4]nonane (0.04 g, 17%): CI-MS m/z 343 ((M+H)+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by chromatography (SiO2, gradient from 20% EtOAc/hex to 100% CH2Cl2)

Sources & evidence

ORD record
ord-9c494be4e8d54a89955c78d0a57afed9
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

Loading…