4-Iodophenol → HCID 11706788, compound

HRID 2057052Notes

Reaction equation

HRID 2057052 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][C:36]([OH:39])=[CH:35][CH:34]=1>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:36]3[CH:37]=[CH:38][C:33]([I:32])=[CH:34][CH:35]=3)[N:7]=2)[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Participants

6

Reactant 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 218970216-chloro-N-(3-chloro-4-methoxyphenyl)-N'-cycloheptyl-[1,3,5]triazine-2,4-diamine

Product 1

HCID 11706788HCID 11706788, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound 133 (2.0 g, 5.22 mmol), potassium carbonate (3.6 g, 26.10 mmol) in dimethylformamide (10 mL) was added 4-iodophenol (1.38 g, 6.26 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 (10-20% EtOAc-Hexane) to afford the title compound as white solid (2.66 g, 90%). mp 80-82° 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 38.47 min, 97.83% 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-0ef87b5b66ea4930aa8b92f27f6c4d69
Source dataset
uspto-grants-2008_02
Patent number
US07335770B2

Reaction notes

Loading…