Diisopropylethylamine → HCID 54671087, compound

HRID 408019Notes

Reaction equation

HRID 408019 reaction equation
[CH3:1][S:2]([C:5]1[N:10]=[CH:9][C:8]([NH:11][C@H:12]2[CH2:16][CH2:15][N:14]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:13]2=[O:23])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Cl:24][C:25]1[CH:30]=[N:29][C:28](Cl)=[CH:27][N:26]=1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[Cl:24][C:25]1[N:26]=[CH:27][C:28]([N:20]2[CH2:21][CH2:22][CH:17]([N:14]3[CH2:15][CH2:16][C@H:12]([NH:11][C:8]4[CH:9]=[N:10][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=4)[C:13]3=[O:23])[CH2:18][CH2:19]2)=[N:29][CH:30]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3362242,5-DichloropyrazineHCID 66800463HCID 66800463, compound

Product 1

HCID 54671087HCID 54671087, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

(S)-3-(6-(Methylsulfonyl)pyridin-3-ylamino)-1-(piperidin-4-yl)pyrrolidin-2-one (0.076 g, 0.22 mmol) and 2,5-dichloropyrazine (0.054 g, 0.36 mmol) were dissolved in NMP (0.45 mL) and treated with DIEA (0.098 mL, 0.56 mmol). The mixture was stirred at 80° C. overnight and then cooled to ambient temperature. The reaction mixture was partitioned between EtOAc (40 mL) and H2O (20 mL). The mixture was filtered through a 0.45 μm nylon membrane and the solids were washed with EtOAc and then dried under high vacuum to provide (S)-1-(1-(5-chloropyrazin-2-yl)piperidin-4-yl)-3-(6-(methylsulfonyl)pyridin-3-ylamino)pyrrolidin-2-one (0.030 g, 0.067 mmol, 30%).

Workup

  1. temperaturecooled to ambient temperature
  2. customThe reaction mixture was partitioned between EtOAc (40 mL) and H2O (20 mL)
  3. filtrationThe mixture was filtered through a 0.45 μm nylon membrane
  4. washthe solids were washed with EtOAc
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-e41ad26699134d04ba5584c77d4c8636
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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