Hydrochloric Acid → HCID 68182505, compound

HRID 1623889Notes

Reaction equation

HRID 1623889 reaction equation
C([O:3][C:4](=[O:14])[C:5](=[C:7]1[CH2:12][C@@H:11]2[C@@H:9]([CH2:10]2)[C:8]1=O)[O-])C.[NH:15]([C:17]1[CH:22]=[N:21][CH:20]=[CH:19][N:18]=1)[NH2:16].Cl>C(O)C.O>[N:18]1[CH:19]=[CH:20][N:21]=[CH:22][C:17]=1[N:15]1[C:8]2[C@@H:9]3[CH2:10][C@@H:11]3[CH2:12][C:7]=2[C:5]([C:4]([OH:3])=[O:14])=[N:16]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14878232-HydrazinopyrazineHCID 866696432-ethoxy-2-oxo-1-((1R,5R)-2-oxobicyclo[3.1.0]hexan-3-ylidene)ethanolate

Product 1

HCID 68182505HCID 68182505, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of 2-ethoxy-2-oxo-1-((1R,5R)-2-oxobicyclo[3.1.0]hexan-3-ylidene)ethanolate (300 mg, 1.28 mmol) in ethanol (5 mL) was added 2-hydrazinylpyrazine (141 mg, 1.28 mmol) followed by 6 N HCl (0.5 mL, 3.0 mmol). The reaction was stirred overnight at room temperature. The reaction was diluted with H2O and extracted with DCM. The combined organic phases were washed with H2O, dried over MgSO4, and concentrated. Purification by silica gel flash chromatography gave the title compound (150 mg). LCMS m/z=271.2 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 0.47 (td, J=4.7 and 3.4 Hz, 1H), 1.22-1.28 (m, 1H), 1.39 (t, J=7.1 Hz, 3H), 2.26-2.30 (m, 1H), 2.77-2.82 (m, 1H), 2.87 (d, J=16.6 Hz, 1H), 2.98 (dd, J=16.6 and 6.3 Hz, 1H), 4.40 (q, J=7.1 Hz, 2H), 8.40 (dd, J=2.6 and 1.5 Hz, 1H), 8.51 (d, J=2.5 Hz, 1H), 9.39 (d, J=1.3 Hz, 1H).

Workup

  1. extractionextracted with DCM
  2. washThe combined organic phases were washed with H2O
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customPurification by silica gel flash chromatography

Sources & evidence

ORD record
ord-8a5193a3386f4227a0297e89698c1364
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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