Acetic Anhydride → HCID 58786333, compound

HRID 1676863Notes

Reaction equation

HRID 1676863 reaction equation
[Li]CCCC.[O:6]1[C:10]2[CH:11]=[CH:12][C:13]([CH2:15][N:16]([CH2:33][C:34]3[CH:42]=[CH:41][C:37]4[O:38][CH2:39][O:40][C:36]=4[CH:35]=3)[CH2:17][C:18]3[N:22]([CH2:23][CH2:24][CH2:25][CH3:26])[CH:21]=[N:20][C:19]=3[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:14][C:9]=2[O:8][CH2:7]1.[CH3:43][C:44](OC(C)=O)=[O:45]>C1COCC1>[O:38]1[C:37]2[CH:41]=[CH:42][C:34]([CH2:33][N:16]([CH2:17][C:18]3[N:22]([CH2:23][CH2:24][CH2:25][CH3:26])[C:21]([C:44](=[O:45])[CH3:43])=[N:20][C:19]=3[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:15][C:13]3[CH:12]=[CH:11][C:10]4[O:6][CH2:7][O:8][C:9]=4[CH:14]=3)=[CH:35][C:36]=2[O:40][CH2:39]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 673709331-(1,3-benzodioxol-5-yl)-N-(1,3-benzodioxol-5-ylmethyl)-N-[(1-butyl-4-phenyl-1H-imidazol-5-yl)methyl]methanamineHCID 178418339Butyllithium

Product 1

HCID 58786333HCID 58786333, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-BuLi (1.2 equivalents in 175 μl hexane) is added to a solution of 1-(1,3-benzodioxol-5-yl)-N-(1,3-benzodioxol-5-ylmethyl)-N-[(1-butyl-4-phenyl-1H-imidazol-5-yl)methyl]methanamine (118 mg), obtained as a minor product in Example 2, step 4, in 10 mL anhydrous THF under N2 at −78° C. The resulting mixture is stirred at −78° C. for 1 hour. Ac2O (118.4 mg, 1.2 equivalents) is added. The reaction mixture is stirred at −78° C. for 2 more hours, warned to room temperature, and stirred overnight. The reaction is quenched with 5 mL of H2O and diluted with 20 mL ethyl acetate. The organic phase is collected, washed with brine, dried and concentrated. Purification via silica gel chromatography provides the title compound (Compound 8).

Workup

  1. stirringThe reaction mixture is stirred at −78° C. for 2 more hours
  2. customwarned to room temperature
  3. stirringstirred overnight
  4. customThe reaction is quenched with 5 mL of H2O
  5. additiondiluted with 20 mL ethyl acetate
  6. customThe organic phase is collected
  7. washwashed with brine
  8. customdried
  9. concentrationconcentrated
  10. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-190d014bb15744dca77e0e3cca7fbcb0
Source dataset
uspto-grants-2011_08
Patent number
US08007767B2

Reaction notes

Loading…