Triethylamine → HCID 23150913, compound

HRID 1984722Notes

Reaction equation

HRID 1984722 reaction equation
C(N(CC)CC)C.Cl[CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([N:16]([CH3:18])[CH3:17])[CH:11]=1.[C:19]([C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:38])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[SH:37])=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20]>CN(C)C=O.C(OCC)(=O)C>[C:19]([C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:38])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[S:37][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([N:16]([CH3:18])[CH3:17])[CH:11]=2)=[CH:25][CH:24]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 23150921HCID 23150921, compoundHCID 23150928HCID 23150928, compound

Product 1

HCID 23150913HCID 23150913, compoundYield 34.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (6 μL, 0.44 mmol) was added to a solution of 4-chloromethyl-2-dimethylaminopyridine (36 mg, 0.21 mmol) and N-(4-tert-butylphenyl)-2-mercaptobenzamide (36 mg, 0.13 mmol) in N,N-dimethylformamide (1.0 mL) at room temperature, and the mixture was stirred for 68 hours. The mixture was diluted with ethyl acetate (30 mL), the whole was washed with saturated aqueous sodium hydrogen carbonate solution (30 mL) and brine (30 mL) successively, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give 19 mg of the target compound as a pale yellow oil. (Yield 22%)

Workup

  1. washthe whole was washed with saturated aqueous sodium hydrogen carbonate solution (30 mL) and brine (30 mL) successively
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7527117d36ff464fac1aedd84bf3f20b
Source dataset
uspto-grants-2009_06
Patent number
US07544703B2

Reaction notes

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