2-Iodophenol → HCID 11685541, compound

HRID 2057053Notes

Reaction equation

HRID 2057053 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+].[I:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[OH:39]>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:39][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[I:32])[N:7]=2)[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Participants

6

Reactant 3

HCID 107842-IodophenolHCID 11430Potassium CarbonateHCID 218970216-chloro-N-(3-chloro-4-methoxyphenyl)-N'-cycloheptyl-[1,3,5]triazine-2,4-diamine

Product 1

HCID 11685541HCID 11685541, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound 133 (1.75 g, 4.57 mmol), potassium carbonate (3.15 g, 22.85 mmol) in dimethylformamide (8 mL) was added 2-iodophenol (1.20 g, 5.48 mmol). It is 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 as white solid (2.45 g, 95%). mp 206-208° 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, 5/60, 15/80, 30/80, 35/60, 40/60; 230 nm, Rt 26.65 min, 98.30% purity; MS (CI): m/z 566 (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-502f4a4b1f93428480c9c2f7c2daf0e2
Source dataset
uspto-grants-2008_02
Patent number
US07335770B2

Reaction notes

Loading…