Ethyl Acetate → HCID 11847516, compound

HRID 1158620Notes

Reaction equation

HRID 1158620 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([OH:10])=O)[CH:2]=1.C(N(CC)C(C)C)(C)C.[CH3:21][C:22]1[C:27]([NH2:28])=[C:26]([CH3:29])[CH:25]=[C:24]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[N:23]=1.C(OCC)(=O)C>CN(C)C=O>[CH3:21][C:22]1[C:27]([NH:28][C:8](=[O:10])[CH2:7][C:3]2[CH:2]=[C:1]([CH3:11])[CH:6]=[CH:5][CH:4]=2)=[C:26]([CH3:29])[CH:25]=[C:24]([N:30]2[CH2:31][CH2:32][O:33][CH2:34][CH2:35]2)[N:23]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 12121m-Tolylacetic acidHCID 81531DiisopropylethylamineHCID 66862754908608-00-4

Product 1

HCID 11847516HCID 11847516, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

m-Tolylacetic acid (0.33 g), N,N-diisopropyl-ethylamine (0.90 mL) and N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-yl-methylene]-N-methyl-methanaminium hexafluoro-phosphate N-oxide (1.00 g) were mixed in dry N,N-dimethylformamide (3 mL) and stirred under argon for 2 minutes. 2,4-Dimethyl-6-morpholin-4-yl-pyridin-3-ylamine (0.30 g) dissolved in dry N,N-dimethylformamide (2 mL) was added to the reaction mixture, which was stirred at 25° C. under argon for 16 hours. Ethyl acetate (20 mL) was added and the organic phase was washed with saturated aqueous ammonium chloride/water (1:1, 20 mL), water (20 mL), brine/water (1:1, 20 mL), dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography (SiO2, heptane/ethylacetate 3:1) to furnish 0.069 g (14% yield) of the title compound as a white solid. LC-MS (m/z) 340 (MH+); tR=1.42, (UV, ELSD) 96%, 100%. 1H NMR (500 MHz, DMSO-d6): 2.00 (s, 3H), 2.11 (s, 3H), 2.29 (s, 3H), 3.37 (m, 4H), 3.56 (s, 2H), 3.67 (m, 4H), 6.52 (s, 1H), 7.06 (d, 1H), 7.15 (m, 2H), 7.21 (t, 1H), 9.30 (s, 1H).

Workup

  1. additionwas added to the reaction mixture, which
  2. stirringwas stirred at 25° C. under argon for 16 hours
  3. washthe organic phase was washed with saturated aqueous ammonium chloride/water (1:1, 20 mL), water (20 mL), brine/water (1:1, 20 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (SiO2, heptane/ethylacetate 3:1)

Sources & evidence

ORD record
ord-57be7c82e0eb4f128903e3d9c16e134b
Source dataset
uspto-grants-2010_10
Patent number
US07812020B2

Reaction notes

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