Diisopropylethylamine → HCID 86688125, compound

HRID 408028Notes

Reaction equation

HRID 408028 reaction equation
[F:1][C:2]1[CH:21]=[C:20]([S:22]([CH3:25])(=[O:24])=[O:23])[C:19]([F:26])=[CH:18][C:3]=1[O:4][C@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:6]1=[O:17].CCN(C(C)C)C(C)C.[Cl:36][C:37]1[CH:42]=[N:41][C:40](Cl)=[CH:39][N:38]=1>CN(C=O)C.CCOC(C)=O>[Cl:36][C:37]1[N:38]=[CH:39][C:40]([N:14]2[CH2:15][CH2:16][CH:11]([N:7]3[CH2:8][CH2:9][CH2:10][C@H:5]([O:4][C:3]4[CH:18]=[C:19]([F:26])[C:20]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:21][C:2]=4[F:1])[C:6]3=[O:17])[CH2:12][CH2:13]2)=[N:41][CH:42]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 3362242,5-DichloropyrazineHCID 66802663(S)-3-(2,5-Difluoro-4-(methylsulfonyl)phenoxy)-1,4'-bipiperidin-2-one

Product 1

HCID 86688125HCID 86688125, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of (S)-3-(2,5-difluoro-4-(methylsulfonyl)phenoxy)-[1,4′-bipiperidin]-2-one (Preparation G; 40 mg, 0.103 mmol), DIEA (90 μL, 0.515 mmol), and 2,5-dichloropyrazine (30.7 mg, 0.206 mmol) in DMF (1 mL) was heated at 100° C. in a sealed tube for 2 hours. The mixture was cooled, diluted with EtOAc (25 mL), washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by preparative TLC (EtOAc/DCM 4:1) to afford (S)-1′-(5-chloropyrazin-2-yl)-3-(2,5-difluoro-4-(methylsulfonyl)phenoxy)-[1,4′-bipiperidin]-2-one (2 mg, 0.004 mmol, 4% yield) as a white solid. Mass spectrum (apci) m/z=501.1 (M+H).

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative TLC (EtOAc/DCM 4:1)

Sources & evidence

ORD record
ord-e0be3162893b490c97fc5ffee73a88fa
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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