2-Fluorophenol → HCID 11597748, compound

HRID 1374035Notes

Reaction equation

HRID 1374035 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.[F:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[OH:33].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Cl:17][C:11]1[CH:10]=[C:9]([NH:8][C:6]2[N:5]=[C:4]([NH:18][CH:19]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[N:3]=[C:2]([O:33][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[F:26])[N:7]=2)[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Participants

6

Reactant 3

HCID 97072-FluorophenolHCID 11430Potassium CarbonateHCID 218970216-chloro-N-(3-chloro-4-methoxyphenyl)-N'-cycloheptyl-[1,3,5]triazine-2,4-diamine

Product 1

HCID 11597748HCID 11597748, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound 133 (0.3 g, 0.785 mmol), 2-fluorophenol (0.106 g, 0.942 mmol) and potassium carbonate (541 mg, 3.93 mmol) in dimethylformamide (3 mL) 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 (10–20% EtOAc-Hexane) to afford the title compound E28 as a pale yellow solid (0.2 g, 56%). mp 98–100° C.; HPLC: Inertsil ODS 3V (250×4.6 mm) 5 microns [solvent A=0.01 M KH2PO4 (pH 7.0); solvent B=CH3CN], Gradient elution program: T/% B=0/60, 10/60, 25/80, 40/80, 45/60, 50/60; 268 nm, Rt 29.79 min, 99.82% purity; MS (CI): m/z 458 (M+H, 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 (10–20% EtOAc-Hexane)

Sources & evidence

ORD record
ord-7dabee41126742e9a33e9670b9125a6b
Source dataset
uspto-grants-2007_01
Patent number
US07163943B2

Reaction notes

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