Diisopropylethylamine → HCID 86692137, compound

HRID 527907Notes

Reaction equation

HRID 527907 reaction equation
[Cl:1][C:2]1[N:9]=[C:8](Cl)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].CCN(C(C)C)C(C)C.[CH3:20][NH:21][C@@H:22]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23]1>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[N:9]=[C:8]([N:21]([CH3:20])[C@@H:22]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])[CH2:23]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 126055382,6-Dichloropyridine-3-carbonitrileHCID 45089543tert-Butyl (3R)-3-(methylamino)pyrrolidine-1-carboxylate

Product 1

HCID 86692137HCID 86692137, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,6-dichloronicotinonitrile (2.2 mmol) and DIPEA (10 mmol) in DMF (10 mL) was added (R)-tert-butyl 3-(methylamino)pyrrolidine-1-carboxylate with stirring at room temperature. The reaction mixture was stirred at 100° C. overnight. Then the mixture was diluted with EtOAc, washed 3 times with water, dried, filtered and concentrated. The crude product was purified by flash chromatography to give the title compound.

Workup

  1. stirringThe reaction mixture was stirred at 100° C. overnight
  2. washwashed 3 times with water
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-ab45bfb89b7c4d57ace4cf1f37a78244
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

Loading…