Formic Acid → HCID 57819944, compound

HRID 1714170Notes

Reaction equation

HRID 1714170 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:10]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)[C:9]2=[O:37])=[CH:4][CH:3]=1.[CH:38]([N-]C(C)C)(C)C.[Li+].CI.C(O)=O.N.O>C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:38])[N:12]([CH2:13][CH2:14][N:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)[CH:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:10]([C:27]3[CH:28]=[CH:29][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:31][CH:32]=3)[C:9]2=[O:37])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 284Formic AcidHCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 12896473Azane;hydrateHCID 57820079HCID 57820079, compound

Product 1

HCID 57819944HCID 57819944, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(4-bromo-phenyl)-1-(2-morpholin-4-yl-ethyl)-2-phenyl-3-(4-trifluoromethyl-phenyl)-imidazolidin-4-one (2.30 g, 4.00 mmol) in anhydrous THF (40 mL) at −78 degrees Celcius was added lithium diisopropylamide (5.3 mL, 1.5M solution of LDA in cyclohexane) and this stirred for 1 h. Methyl iodide (1.13 g, 8.00 mmol) was then added at −78 degrees Celcius and the reaction allowed to warm to room temperature over 2 hours. The reaction was then quenched with 2 equivalents of formic acid followed by NH3.H2O to basify the solution, diluted with ethyl acetate, washed with water and brine, and then dried over Na2SO4. After filtering and concentrating in vacuo, the crude product was purified by flash column chromatography eluting with ethyl acetate:petroleum ether gradient (10%-50%) to afford the product as a pale yellow solid (1.0 g, 43%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtering
  4. concentrationconcentrating in vacuo
  5. customthe crude product was purified by flash column chromatography
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-6fbced07b38442e3bba47e97fff27a4d
Source dataset
uspto-grants-2010_09
Patent number
US07795315B2

Reaction notes

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