Water → HCID 54671335, compound

HRID 2207851Notes

Reaction equation

HRID 2207851 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-56fcb5ce1d1a45d5837213843e8866fd
Source dataset
uspto-grants-2016_06
Patent number
US09376450B2

Reaction notes

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