Water → HCID 67536094, compound

HRID 1486814Notes

Reaction equation

HRID 1486814 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.CCN(CC)CC.[NH2:19][CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.O>O1CCOCC1.[Cl-].[Na+].O>[O:23]1[CH2:24][CH2:25][CH:20]([NH:19][C:2]2[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=2)[CH2:21][CH2:22]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 406081Methyl 5-chloropyrazine-2-carboxylateHCID 4192234-Aminotetrahydropyran

Product 1

HCID 67536094HCID 67536094, compoundYield 33.9%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 5-chloro-2-pyrazinecarboxylate (507 mg, 2.94 mmol), Et3N (1.08 mL, 7.64 mmol) and 4-aminotetrahydropyran (0.40 mL, 3.82 mmol) were dissolved in dioxane (5 mL) and heated in a microwave reactor at 100° C. for 20 min. Water (50 mL) and brine (25 mL) were added and the reaction mixture was extracted into EtOAc (2×100 mL), dried (MgSO4) and concentrated in vacuo to give the title compound (236 mg, 33.9%) as a yellow oil. LCMS (ES+): 238.2 [MH]+.

Workup

  1. extractionthe reaction mixture was extracted into EtOAc (2×100 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-503db6c51ea74e10975947394d31f2c2
Source dataset
uspto-grants-2016_08
Patent number
US09428498B2

Reaction notes

Loading…