Acetonitrile → HCID 178501201, compound

HRID 518594Notes

Reaction equation

HRID 518594 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][C@@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]([O:20][CH2:21]C)=[O:19])[CH2:14][CH2:13]1.C(#N)C.CCN(C(C)C)C(C)C>O.C(Cl)Cl>[N+:8]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[NH:11][C@@H:12]1[CH2:13][CH2:14][C@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:16][CH2:17]1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 27357814-Chloro-3-nitropyridineHCID 178472433HCID 178472433, compound

Product 1

HCID 178501201HCID 178501201, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A round bottom flask under nitrogen atmosphere was charged with 4-chloro-3-nitropyridine (1.65 g, 10.41 mmol), cis-ethyl 4-aminocyclohexanecarboxylate (2.454 g, 15.61 mmol), and ACN (26 mL). To the mixture was added DIPEA (3.63 mL, 20.81 mmol). The resulting mixture was stirred at 60° C. for 17 hours. The reaction was stopped, cooled to RT and diluted with water (20 mL) and DCM (50 mL). The layers were separated, and the organic layer was collected, dried over sodium sulfate and concentrated to afford an orange oil. The oil was purified by silica gel chromatography to afford the title compound (2.2 g, 76% yield) as a bright yellow solid. MS m/z=280.2 [M+H]. Calc'd for C13H17N3O4: 279.1.

Workup

  1. temperaturecooled to RT
  2. customThe layers were separated
  3. customthe organic layer was collected
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto afford an orange oil
  7. customThe oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-60184fe277274f098705ff142f38a7af
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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