Potassium Carbonate → HCID 11606009, compound

HRID 2057056Notes

Reaction equation

HRID 2057056 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([Cl:17])[CH:10]=2)[N:5]=[C:4]([NH:18][CH:19]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:32][C:33]([C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[C:37]([Cl:42])[CH:36]=1)=[O:34]>CN(C)C=O.O>[Cl:42][C:37]1[CH:36]=[C:35]([C:33](=[O:34])[CH3:32])[CH:40]=[CH:39][C:38]=1[O:41][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([Cl:17])[CH:10]=2)[N:5]=[C:4]([NH:18][CH:19]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10515141-(3-Chloro-4-hydroxyphenyl)ethanoneHCID 218970216-chloro-N-(3-chloro-4-methoxyphenyl)-N'-cycloheptyl-[1,3,5]triazine-2,4-diamine

Product 1

HCID 11606009HCID 11606009, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound 133 (0.30 g, 0.78 mmol), potassium carbonate (0.54 g, 3.92 mmol) in dimethylformamide (10 mL) was added 3-chloro-4-hydroxyacetophenone (0.133 g, 0.78 mmol). It was heated to 80° C. for 12 hours with stirring under nitrogen atmosphere. The mixture was then cooled, diluted with water (20 mL) and extracted with EtOAc (2×20 mL). The combined organic layers were washed with water (2×10 mL), dried over anhydrous sodium sulphate and concentrated under vacuum. The residue thus obtained was purified by column chromatography to afford the title compound as white solid (0.08 g, 67%). mp 186-196° C.; HPLC: Inertsil ODS 3V (250×4.6 mm) 5 microns [mobile phase: 0.01 M KH2PO4: CH3CN (20:80)]; 212 nm, R, 12.33 min, 99.15% purity; MS (CI): m/z 516 (M+, 100).

Workup

  1. temperatureThe mixture was then cooled
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined organic layers were washed with water (2×10 mL)
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under vacuum
  6. customThe residue thus obtained
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-5a97656064ac4e1d8d520cfaaac024ce
Source dataset
uspto-grants-2008_02
Patent number
US07335770B2

Reaction notes

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