Trimethylamine → HCID 57566938, compound

HRID 1727156Notes

Reaction equation

HRID 1727156 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]1[CH2:14][N:13]([C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18]([NH2:20])=[O:19])[C:12](=[O:24])[CH2:11]1.[Cl:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1.N(C)(C)C>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:25][C:26]1[CH:31]=[C:30]([CH:29]=[CH:28][CH:27]=1)[O:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]1[CH2:14][N:13]([C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18]([NH2:20])=[O:19])[C:12](=[O:24])[CH2:11]1

Participants

6

Reactant 3

HCID 1146TrimethylamineHCID 2734323(3-Chlorophenyl)boronic acidHCID 68828392HCID 68828392, compound

Product 1

HCID 57566938HCID 57566938, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

3-[4-(2-Hydroxy-4-methoxyphenyl)-2-oxo-pyrrolidin-1-yl]benzamide (32 mg, 0.1 mmol), 3-chlorobenzeneboronic acid (19 mg, 1.2 eq), and copper acetate (1 eq) were added to a dry tube. The mixture was charged with 2 mL CH2Cl2, (CH3)3N (3 eq) followed by addition of 4 Å MS. The mixture was stirred for 24 h and diluted with 10 mL CH2Cl2. After filtration, the mixture was washed with NH4Cl, water, and brine, and then dried. After concentration, the residue was purified by preparative LC-MS to give 7.8 mg of the desired product. Yield: 18%.

Workup

  1. additionfollowed by addition of 4 Å MS
  2. filtrationAfter filtration
  3. washthe mixture was washed with NH4Cl, water, and brine
  4. customdried
  5. concentrationAfter concentration
  6. customthe residue was purified by preparative LC-MS

Sources & evidence

ORD record
ord-b1a5c42a9493438f954a31edd1c74162
Source dataset
uspto-grants-2009_02
Patent number
US07495016B2

Reaction notes

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