Diisopropylethylamine → HCID 86688097, compound

HRID 407941Notes

Reaction equation

HRID 407941 reaction equation
Cl.[F:2][C:3]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[C:5]([F:13])[C:4]=1[NH:14][C@H:15]1[CH2:20][CH2:19][CH2:18][N:17]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[C:16]1=[O:27].[Cl:28][C:29]1[CH:34]=[N:33][C:32](Cl)=[CH:31][N:30]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:28][C:29]1[N:30]=[CH:31][C:32]([N:24]2[CH2:23][CH2:22][CH:21]([N:17]3[CH2:18][CH2:19][CH2:20][C@H:15]([NH:14][C:4]4[C:3]([F:2])=[CH:8][C:7]([S:9]([CH3:12])(=[O:11])=[O:10])=[CH:6][C:5]=4[F:13])[C:16]3=[O:27])[CH2:26][CH2:25]2)=[N:33][CH:34]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3362242,5-DichloropyrazineHCID 67470549HCID 67470549, compound

Product 1

HCID 86688097HCID 86688097, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A flask was charged with (S)-3-(2,6-difluoro-4-(methylsulfonyl)phenylamino)-1,4′-bipiperidin-2-one hydrochloride (0.250 g, 0.590 mmol), 2,5-dichloropyrazine (0.105 g, 0.708 mmol), Hunig's base (0.309 mL, 1.77 mmol), and DMF (5 mL). The reaction mixture was stirred at 100° C. overnight. The organic solvents were removed under reduced pressure. The residue was purified using silica gel column chromatography eluting with ethyl acetate to provide (S)-1′-(5-chloropyrazin-2-yl)-3-(2,6-difluoro-4-(methylsulfonyl)phenylamino)-[1,4′-bipiperidin]-2-one (0.102 g, 0.204 mmol, 34.6% yield) as light yellow solid. Mass spectrum (apci) m/z=500.1 (M+H).

Workup

  1. customThe organic solvents were removed under reduced pressure
  2. customThe residue was purified
  3. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-8194668a38594e0f88e96ebf2a3c8ae6
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

Loading…