Triethylamine → HCID 89444921, compound

HRID 1522529Notes

Reaction equation

HRID 1522529 reaction equation
N/[C:2](/[CH3:6])=[CH:3]\[C:4]#[N:5].[CH:7]1([NH:10][NH2:11])[CH2:9][CH2:8]1.C(N(CC)CC)C>C(O)C>[CH:7]1([N:10]2[C:4]([NH2:5])=[CH:3][C:2]([CH3:6])=[N:11]2)[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 19594968Cyclopropylhydrazine

Product 1

HCID 89444921HCID 89444921, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

(2Z)-3-amino-2-butenenitrile (903 mg, 11.00 mmol), cyclopropylhydrazine (1194 mg, 11 mmol) and triethylamine (3.07 mL, 22.00 mmol) were suspended in ethanol (100 mL) and heated to 70° C. for 16 hours. The solvent was removed in vacuo. The residue was suspended in 50 mL of saturated NaHCO3 and stirred for 10 minutes. The contents were extracted with DCM, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (eluent: 0% to 100% gradient EtOAc:Hex). The product was collected as 310 mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.95-1.13 (m, 4 H), 2.13 (s, 3 H), 3.06 (m, J=6.95, 6.95, 3.79, 3.54 Hz, 1 H), 3.76-3.88 (m, 2 H), 5.24 (s, 1 H). LCMS(ES) [M+H]+ 138.1

Workup

  1. customThe solvent was removed in vacuo
  2. extractionThe contents were extracted with DCM
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (eluent: 0% to 100% gradient EtOAc:Hex)
  7. customThe product was collected as 310 mg

Sources & evidence

ORD record
ord-0c6820c37a1c446493dc1edb30d8a715
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

Loading…