Trimethylamine → 3-{4-[3-(2-Cyanophenoxy)phenyl]-2-oxo-pyrrolidin-1-yl}benzamide

HRID 1819351Notes

Reaction equation

HRID 1819351 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:12][N:11]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=3)[C:16]([NH2:18])=[O:17])[C:10](=[O:22])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O)#[N:24].N(C)(C)C>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:12][N:11]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=3)[C:16]([NH2:18])=[O:17])[C:10](=[O:22])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1)#[N:24]

Participants

6

Reactant 3

HCID 1146TrimethylamineHCID 27346102-Cyanophenylboronic acidHCID 688283783-[4-(3-Hydroxyphenyl)-2-oxo-pyrrolidin-1-yl]benzamide

Product 1

HCID 688325043-{4-[3-(2-Cyanophenoxy)phenyl]-2-oxo-pyrrolidin-1-yl}benzamideYield 43.1%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-[4-(3-hydroxyphenyl)-2-oxo-pyrrolidin-1-yl]benzamide (30 mg), 2-cyanobenzeneboronic acid (12 mg), and copper acetate (2 eq) was created in a dry tube. The mixture was dissolved in 2 mL CH2Cl2 followed by the addition of (CH3)3N (3 eq). The mixture was stirred at r.t. for 24 h, and then diluted with 10 mL CH2Cl2. The resulting mixture was filtered and washed with NH4Cl solution, water and brine. After removal of solvent, the residue was purified by preparative LC-MS to give 14 mg of the desired product. Yield: 35%.

Workup

  1. customwas created in a dry tube
  2. filtrationThe resulting mixture was filtered
  3. washwashed with NH4Cl solution, water and brine
  4. customAfter removal of solvent
  5. customthe residue was purified by preparative LC-MS

Sources & evidence

ORD record
ord-c54a0939a9754739b963499cb54e3d6d
Source dataset
uspto-grants-2009_10
Patent number
US07601742B2

Reaction notes

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