Tetrahydrofuran → HCID 68311090, compound

HRID 470713Notes

Reaction equation

HRID 470713 reaction equation
[CH3:1][NH2:2].O1CCCC1.O1CCCC1.N1(O[C:23](=[O:39])[CH2:24][C@H:25]2[O:30][CH2:29][C@H:28]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:27][CH2:26]2)C2C=CC=CC=2N=N1>C(OCC)(=O)C>[CH3:1][NH:2][C:23](=[O:39])[CH2:24][C@H:25]1[O:30][CH2:29][C@H:28]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 66615946Methylamine tetrahydrofuranHCID 86672615HCID 86672615, compound

Product 1

HCID 68311090HCID 68311090, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methylamine/tetrahydrofuran solution (2.0 mol/l, 1 ml) was added to a tetrahydrofuran (5 ml) solution of the compound (378 mg, 1.00 mmol) obtained in Step 1 above and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate, washed with water, saturated sodium bicarbonate solution, and brine in that order and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography [methanol:ethyl acetate=5:95 (v/v)] to give 135 mg (49%) of the title compound as a solid.

Workup

  1. washwashed with water, saturated sodium bicarbonate solution, and brine in that order
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue obtained
  5. customwas purified by silica gel column chromatography [methanol:ethyl acetate=5:95 (v/v)]

Sources & evidence

ORD record
ord-bcc6cec5d1f14edb8cd108f447655d3e
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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