Triethylamine → HCID 117839832, compound

HRID 1477704Notes

Reaction equation

HRID 1477704 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[CH:12]=[N:11][C:10]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[N:9][C:8]2=[O:19])=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1.[Cl-].[NH4+]>C(OCC)(=O)C.CN(C)C=O>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[CH:12]=[N:11][C:10]([N:13]3[CH2:18][CH2:17][N:16]([C:34](=[O:35])[C:33]4[CH:37]=[CH:38][C:30]([F:29])=[CH:31][CH:32]=4)[CH2:15][CH2:14]3)=[N:9][C:8]2=[O:19])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 678794-Fluorobenzoyl chlorideHCID 117839396HCID 117839396, compound

Product 1

HCID 117839832HCID 117839832, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an N,N-dimethylformamide solution (1 mL) of 1-(4-chlorobenzyl)-4-(piperazin-1-yl)-1,3,5-triazin-2(1H)-one (31 mg, 0.10 mmol) synthesized in Reference Synthesis Example 9, triethylamine (28 μL, 0.20 mmol) and 4-fluorobenzoyl chloride (18 μL, 0.15 mmol) were added at room temperature and the resultant mixture was stirred at room temperature for 4 hours. After the completion of the reaction, saturated ammonium chloride aqueous solution was added to the reaction solution and extraction with ethyl acetate from the resultant reaction solution was performed. The organic layer was concentrated under reduced pressure and the resultant residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/4→0/1 (v/v)) to obtain the title compound (27 mg, yield: 63%).

Workup

  1. additionwere added at room temperature
  2. customreaction solution
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe resultant residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/4→0/1 (v/v))

Sources & evidence

ORD record
ord-a5b3ac9781f440cb9f0517c5aab4ac3c
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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