Dimethylformamide → HCID 117839541, compound

HRID 1477705Notes

Reaction equation

HRID 1477705 reaction equation
CN(C)C=O.[Cl:6][C:7]1[CH:26]=[CH:25][C:10]([CH2:11][N:12]2[CH:17]=[N:16][C:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[N:14][C:13]2=[O:24])=[CH:9][CH:8]=1.Cl[C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][N:29]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[Cl:6][C:7]1[CH:26]=[CH:25][C:10]([CH2:11][N:12]2[CH:17]=[N:16][C:15]([N:18]3[CH2:23][CH2:22][N:21]([C:28]4[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][N:29]=4)[CH2:20][CH2:19]3)=[N:14][C:13]2=[O:24])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 117839396HCID 117839396, compound

Product 1

HCID 117839541HCID 117839541, compoundYield 4.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

An N,N-dimethylformamide suspension (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, 2-chloro-5-nitropyridine (16 mg, 0.10 mmol) and potassium carbonate (18 mg, 0.20 mmol) was stirred at 100° C. for 1 hour. After the completion of the reaction, water was added to the reaction solution and extraction with ethyl acetate from the resultant reaction solution was performed three times. The organic layer was washed with brine, was dried over anhydrous sodium sulfate, and was concentrated under reduced pressure. The resultant residue was purified by preparative silica gel thin-layer chromatography to obtain the title compound (2.1 mg, yield: 4.9%).

Workup

  1. customreaction solution
  2. washThe organic layer was washed with brine
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. concentrationwas concentrated under reduced pressure
  5. customThe resultant residue was purified by preparative silica gel thin-layer chromatography

Sources & evidence

ORD record
ord-c1a1283f3a1547788cab1c5db22ec7ae
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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