Diisopropylethylamine → HCID 54670052, compound

HRID 408029Notes

Reaction equation

HRID 408029 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[C:37]1[N:42]=[CH:41][C:40]([CH2:43][CH3:44])=[CH:39][N:38]=1>CN(C=O)C.CCOC(C)=O>[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][N:14]([C:37]3[N:42]=[CH:41][C:40]([CH2:43][CH3:44])=[CH:39][N:38]=3)[CH2:13][CH2:12]2)[C:6]1=[O:17]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 35727632-Chloro-5-ethylpyrimidineHCID 66802663(S)-3-(2,5-Difluoro-4-(methylsulfonyl)phenoxy)-1,4'-bipiperidin-2-one

Product 1

HCID 54670052HCID 54670052, compoundYield 38.3%

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; 18 mg, 0.047 mmol), DIEA (24 μL mL, 0.14 mmol), and 2-chloro-5-ethylpyrimidine (20 mg, 0.14 mmol) in DMF (1 mL) was heated at 100° C. for 2 hours in a sealed tube. 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)-3-(2,5-difluoro-4-(methylsulfonyl)phenoxy)-1′-(5-ethylpyrimidin-2-yl)-[1,4′-bipiperidin]-2-one (9 mg, 0.018 mmol, 38% yield) as a white solid. Mass spectrum (apci) m/z=495.1.

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-cd508206a9954261abb346509d72b171
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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