Methyl iodide → HCID 90387398, compound

HRID 1476846Notes

Reaction equation

HRID 1476846 reaction equation
[C:1]([C:3]1[N:4]=[C:5]([NH:13][C@H:14]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]2)[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].[H-].[Na+].[CH3:28]I>CN(C=O)C.CCOC(C)=O>[C:1]([C:3]1[N:4]=[C:5]([N:13]([CH3:28])[C@H:14]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]2)[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 90386987HCID 90386987, compound

Product 1

HCID 90387398HCID 90387398, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To (S)-tert-butyl 3-((3-cyanoisoquinolin-1-yl)amino)pyrrolidine-1-carboxylate (235 mg, 0.694 mmol) in DMF (6 mL) was added NaH (27.8 mg, 0.694 mmol) and methyl iodide (0.052 mL, 0.833 mmol) at 0° C. The reaction mixture was allowed to warm to RT with stirring over a 2 hour period and was subsequently diluted with EtOAc and washed with aqueous NH4Cl, water, and brine. The organic layer was dried over Na2SO4, filtered, and concentrated. Toluene (2×5 mL) was added and removed in vacuo to give the title compound as a crude residue.

Workup

  1. washwashed with aqueous NH4Cl, water, and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionToluene (2×5 mL) was added
  6. customremoved in vacuo

Sources & evidence

ORD record
ord-be4583b66d38409fbe28ca1ec9466667
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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