HCID 13849791, compound → HCID 10437199, compound

HRID 1676861Notes

Reaction equation

HRID 1676861 reaction equation
[Li][CH2:2]CCC.[O:6]1[C:10]2[CH:11]=[CH:12][C:13]([CH2:15][N:16]([CH2:27][C:28]3[N:32]([CH2:33][CH2:34][CH2:35][CH3:36])[CH:31](I)[NH:30][C:29]=3[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][CH3:26])[CH:19]=3)=[CH:14][C:9]=2[O:8][CH2:7]1.C(S([C:54]#[N:55])(=O)=O)C1C=CC=CC=1>C1COCC1>[CH2:33]([N:32]1[C:28]([CH2:27][N:16]([CH2:15][C:13]2[CH:12]=[CH:11][C:10]3[O:6][CH2:2][CH2:7][O:8][C:9]=3[CH:14]=2)[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][CH3:26])[CH:19]=2)=[C:29]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:30]=[C:31]1[C:54]#[N:55])[CH2:34][CH2:35][CH3:36]

Participants

5

Reactant 3

HCID 13849791HCID 13849791, compoundHCID 67372283HCID 67372283, compoundHCID 178418339Butyllithium

Product 1

HCID 10437199HCID 10437199, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-BuLi (1.6 M in 0.2 mL hexane) is added dropwise to a solution of 200 mg of benzo[1,3]dioxol-5-ylmethyl-(1-butyl-2-iodo-4-phenyl-3H-imidazol-5-ylmethyl)-(3-ethoxy-benzyl)-amine (prepared by the procedure set forth in the preceding example) at −78° C. under N2. The resulting mixture is stirred at −78° C. A solution of benzylsulfonyl cyanide (63 mg) in 5 mL THF is added and the resulting mixture is stirred at −78° C. for 2 hours, then warmed to room temperature and stirred overnight. The reaction is quenched with 5.0 mL water, extracted with ethyl acetate, and dried over Na2SO4. Concentration and purification via flash chromatography provides the desired product (Compound 5).

Workup

  1. customprepared by the procedure
  2. customat −78° C.
  3. stirringthe resulting mixture is stirred at −78° C. for 2 hours
  4. temperaturewarmed to room temperature
  5. stirringstirred overnight
  6. customThe reaction is quenched with 5.0 mL water
  7. extractionextracted with ethyl acetate
  8. dry with materialdried over Na2SO4
  9. concentrationConcentration and purification via flash chromatography

Sources & evidence

ORD record
ord-078cd4fbb77749f38609f5809b7e9062
Source dataset
uspto-grants-2011_08
Patent number
US08007767B2

Reaction notes

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