Water → HCID 54671335, compound

HRID 454953Notes

Reaction equation

HRID 454953 reaction equation
Cl.Cl.Cl.Cl[C:5]1([C:11]2[C:12]([O:17][CH:18]3[CH2:21][N:20]([C:22]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:23])[CH2:19]3)=[N:13][CH:14]=[CH:15][N:16]=2)[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[C:32](N1C=CN=C1)(=[O:34])[CH3:33].CCN(C(C)C)C(C)C.[OH2:49]>C(Cl)Cl>[C:32]([N:8]1[CH2:9][CH2:10][C:5]([C:11]2[C:12]([O:17][CH:18]3[CH2:21][N:20]([C:22]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:23])[CH2:19]3)=[N:13][CH:14]=[CH:15][N:16]=2)([OH:49])[CH2:6][CH2:7]1)(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 171741-(1H-Imidazol-1-yl)ethanone2×HCID 81531DiisopropylethylamineHCID 67477388HCID 67477388, compound

Product 1

HCID 54671335HCID 54671335, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of benzyl 3-((3-(4-chloropiperidin-4-yl)pyrazin-2-yl)oxy)azetidine-1-carboxylate trihydrochloride salt, 1-acetylimidazole (0.204 g, 1.851 mmol), DIEA (1.58 mL, 9.25 mmol), and 1-acetylimidazole (0.204 g, 1.851 mmol) in DCM (10 mL) was stirred at room temperature for 16 hours. H2O was added, and layers were separated. The organic extracts were dried over Na2SO4, concentrated and purified by silica gel chromatography using ISCO™ (0-60% EtOAc/Hexanes) to give the title compound. MS (M+1): 427 calc.

Workup

  1. customlayers were separated
  2. dry with materialThe organic extracts were dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-378402432d1f4cf3a743af649e404fa7
Source dataset
uspto-grants-2013_07
Patent number
US08497265B2

Reaction notes

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