1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 90426706, compound

HRID 2278997Notes

Reaction equation

HRID 2278997 reaction equation
C=C(O[C:5](=[O:13])[NH:6][CH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)C.C1CCN2[C:17](=[N:18]CCC2)[CH2:16][CH2:15]1.C(N)C#C>O1CCOCC1.[Cl-].[Na+].O>[CH2:17]([NH:18][C:5]([NH:6][CH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1)=[O:13])[C:16]#[CH:15]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 239041PropargylamineHCID 131733476HCID 131733476, compound

Product 1

HCID 90426706HCID 90426706, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

A solution of prop-1-en-2-yl(tetrahydro-2H-pyran-4-yl)carbamate (0.50 g, 2.70 mmol) in dioxane (20 mL) was treated with DBU (0.1 mL) and propargylamine (0.149 g, 2.70 mmol) and heated at 90° C. overnight. The mixture was cooled to RT, treated with brine and extracted with EtOAc (3×). The combined organics were dried over Na2SO4, concentrated to dryness, treated with Et2O and the resulting solid collected via filtration to afford 1-(prop-2-yn-1-yl)-3-(tetrahydro-2H-pyran-4-yl)urea (400 mg, 81%). 1H NMR (400 MHz, DMSO-d6): δ 6.00 (m, 1 H), 5.99 (m, 1 H), 3.76 (m, 2 H), 3.75 (m, 2 H), 3.56 (m, 1 H), 3.30 (m, 2 H), 3.02 (t, J=2.5 Hz, 1 H), 1.68 (m, 2 H), 1.29 (m, 2H); MS (ESI) m/z: 183.1 (M+H+).

Workup

  1. temperatureThe mixture was cooled to RT
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. additiontreated with Et2O
  6. filtrationthe resulting solid collected via filtration

Sources & evidence

ORD record
ord-fa9d4c420bd04b789466d081b9cf1b0b
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

Loading…