Ethyl Acetate → HCID 11661216, compound

HRID 905593

Reaction equation

HRID 905593 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][C:9]([OH:11])=O.C(N(CC)C(C)C)(C)C.[CH3:21][C:22]1[CH:27]=[C:26]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH:25]=[C:24]([C:34]([F:37])([F:36])[F:35])[C:23]=1[NH2:38].C(OCC)(=O)C>CN(C)C=O>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][C:9]([NH:38][C:23]1[C:24]([C:34]([F:35])([F:36])[F:37])=[CH:25][C:26]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[CH:27][C:22]=1[CH3:21])=[O:11]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 79139Norborn-2-ylacetic acidHCID 81531DiisopropylethylamineHCID 67406600HCID 67406600, compound

Product 1

HCID 11661216HCID 11661216, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Bicyclo[2.2.1]hept-2-yl-acetic acid (160 mg), N,N-diisopropyl-ethylamine (0.44 mL) and N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-yl-methylene]-N-methyl-methanaminium hexafluoro-phosphate N-oxide (0.47 g) were mixed in dry N,N-dimethylformamide (3 mL) and stirred under argon for 2 minutes. 2-Methyl-4-morpholin-4-yl-6-trifluoromethyl-phenylamine (0.18 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 magnesium sulfate, concentrated in vacuo and purified by flash chromatography to furnish 16 mg (6% yield) of the title compound as a white solid. LC-MS (m/z) 397 (MH+); tR=3.12, (UV, ELSD) 91%, 98%.

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 magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c37c53cd227a428fb856985f902a1658
Source dataset
uspto-grants-2011_09
Patent number
US08012962B2

Linked notes

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