Ethanol → HCID 10899819, compound

HRID 1813926Notes

Reaction equation

HRID 1813926 reaction equation
S([O-])(=O)(=[O:3])C.C[NH:7][CH3:8].[CH2:9]1[CH2:13][O:12][CH2:11][CH2:10]1.[CH2:14]([N:16]([CH2:19]C)[CH2:17][CH3:18])C.[CH3:21][CH2:22]O>>[CH3:19][N:16]([CH2:17][C:18]1[CH:22]=[CH:21][C:10]([C:11]([O:12][CH2:13][CH3:9])=[O:3])=[CH:8][N:7]=1)[CH3:14]

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 85257MethanesulfonateHCID 22320367Dimethylamine tetrahydrofuran

Product 1

HCID 10899819HCID 10899819, compoundYield 82%

Conditions

Temperature
80 °C

Procedure

Methanesulfonyl chloride (186 μL, 2.4 mmol) was added dropwise to a cooled (0° C.) CH2Cl2 solution (8 mL) containing 14b (362 mg, 2.0 mmol) and triethylamine (334 μL, 2.4 mmol) under Ar, and then the solution was stirred at 0-5° C. (1 h). CH2Cl2 (10 mL) was added to the reaction and the organic phase was successively washed with a saturated aqueous NaHCO3 solution (10 mL) and brine (2×10 mL), dried (Na2SO4), filtered and evaporated to give mesylate 14d (508 mg, 98%). Compound 14d was combined with a 2 M dimethylamine THF solution (10 mL, 20 mmol) and triethylamine (279 μL, 2.0 mmol) in EtOH (15 mL) and heated at 80° C. (15 h). The reaction solution was concentrated in vacuo and the residue taken up in CH2Cl2 (10 mL). The organic solution was washed with H2O (2×10 mL) and brine (2×10 mL), dried (Na2SO4), filtered and evaporated. The crude product was purified by PTLC (EtOAc) to give 14e (342 mg, 82%) as a yellow oil: Rf 0.17 (EtOAc/hexanes=3/1); IR (neat) 2976, 2821, 2776, 1723, 1599, 1459, 1376, 1282, 1117 cm−1; 1H NMR (CDCl3) δ 1.41 (t, J=7.2 Hz, 3H), 2.31 (s, 6H), 3.65 (s, 2H), 4.41 (q, J=7.2 Hz, 2H), 7.51 (d, J=7.8 Hz, 1H), 8.27 (dd, J=2.1, 7.8 Hz, 1H), 9.16 (d, J=2.1 Hz, 1H); 13C NMR (CDCl3) 14.2, 45.5 (2C), 61.2, 65.4, 122.4, 124.7, 137.3, 150.3, 163.5, 165.2 ppm; MS (+CI) 209 [M+1]+; Mr (+CI) 209.129 93 [M+1]+ (calcd for C11H17N2O2 209.129 00).

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. washThe organic solution was washed with H2O (2×10 mL) and brine (2×10 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by PTLC (EtOAc)

Sources & evidence

ORD record
ord-b028b0b7cbd147f8840c3013953c1e43
Source dataset
uspto-grants-2005_04
Patent number
US06875774B2

Reaction notes

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