HCID 11091715, compound → HCID 10863673, compound

HRID 1594881Notes

Reaction equation

HRID 1594881 reaction equation
[CH2:1]([C:3]1([C:12]2[CH:13]=[C:14]([CH:32]=[CH:33][CH:34]=2)[O:15][C:16]2[CH:23]=[C:22]([C:24]([C:26]3[N:27]([CH3:31])[CH:28]=[N:29][CH:30]=3)=[O:25])[CH:21]=[CH:20][C:17]=2[C:18]#[N:19])[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([CH3:10])[C:4]1=[O:11])[CH3:2].[CH3:35][Mg+].[Br-]>C1COCC1>[CH2:1]([C:3]1([C:12]2[CH:13]=[C:14]([CH:32]=[CH:33][CH:34]=2)[O:15][C:16]2[CH:23]=[C:22]([C:24]([OH:25])([C:26]3[N:27]([CH3:31])[CH:28]=[N:29][CH:30]=3)[CH3:35])[CH:21]=[CH:20][C:17]=2[C:18]#[N:19])[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([CH3:10])[C:4]1=[O:11])[CH3:2]

Participants

4

Reactant 2

HCID 11091715HCID 11091715, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 10863673HCID 10863673, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[3-(3-Ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-(3-methyl-3H-imidazole-4-carbonyl)-benzonitrile (Example 19) (0.216 g, 0.473 mmol) was dissolved in anhydrous THF (10 mL) and a 3.0 M solution of MeMgBr (1.10 mL, 3.30 mmol) was added and stirred at RT. The reaction was quenched with NH4Cl after 1 h, concentrated, diluted with EtOAc, washed with satd. NaHCO3 solution, water, brine, dried (MgSO4), concentrated and purified using SiO2 chromatography (1-3% MeOH/CH2Cl2 w/NH4OH) to give the title compound. FT/ICR MS (M+1)=473.

Workup

  1. customThe reaction was quenched with NH4Cl after 1 h
  2. concentrationconcentrated
  3. additiondiluted with EtOAc
  4. washwashed with satd
  5. dry with materialNaHCO3 solution, water, brine, dried (MgSO4)
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-73181301280a4e7ab3f2c150ab79196b
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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