Triethylamine → HCID 21022367, compound

HRID 1794601Notes

Reaction equation

HRID 1794601 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][CH:12]([C:15]1[N:16]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:17](=[O:28])[C:18]2[C:23]([C:24]([F:27])([F:26])[F:25])=[N:22][O:21][C:19]=2[N:20]=1)[CH2:13][CH3:14])([CH3:4])([CH3:3])[CH3:2].[CH3:37][C:38]1[CH:46]=[CH:45][C:41]([C:42](Cl)=[O:43])=[CH:40][CH:39]=1.CCN(CC)CC>C(Cl)Cl>[C:1]([O:5][C:6](=[O:36])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH:12]([C:15]1[N:16]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:17](=[O:28])[C:18]2[C:23]([C:24]([F:26])([F:25])[F:27])=[N:22][O:21][C:19]=2[N:20]=1)[CH2:13][CH3:14])[C:42](=[O:43])[C:41]1[CH:45]=[CH:46][C:38]([CH3:37])=[CH:39][CH:40]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 134054-Methylbenzoyl Chloride2×HCID 21022366HCID 21022366, compound

Product 1

HCID 21022367HCID 21022367, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 11 (60 mg, 0.118 mmol) in CH2Cl2 (2.0 mL) stirred at room temperature was added 4-methyl-benzoyl chloride (24.1 mg, 0.153 mmol), followed by Et3N (18 mg, 0.117 mmol). The reaction mixture was stirred at room temperature for 1 h. More 4-methyl-benzoyl chloride (24 mg, 0.153 mmol), and Et3N (18 mg, 0.117 mmol) were added. After another hour, the reaction mixture was purified by SiO2 chromatography directly (EtOAc:heaxanes/1:4) to afford 12 (52 mg, 70%). MS (ESI): 628 (M+H)+.

Workup

  1. waitAfter another hour
  2. customthe reaction mixture was purified by SiO2 chromatography directly (EtOAc:heaxanes/1:4)

Sources & evidence

ORD record
ord-48806d206ded4a5ab7b6681d088760a9
Source dataset
uspto-grants-2006_04
Patent number
US07022850B2

Reaction notes

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