4-Hydroxybenzaldehyde → HCID 11612454, compound

HRID 2057055Notes

Reaction equation

HRID 2057055 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+].[OH:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=[O:38])=[CH:35][CH:34]=1>CN(C)C=O.O>[Cl:17][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[O:15][CH3:16])[NH:8][C:6]1[N:5]=[C:4]([NH:18][CH:19]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[N:3]=[C:2]([O:32][C:33]2[CH:40]=[CH:39][C:36]([CH:37]=[O:38])=[CH:35][CH:34]=2)[N:7]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 218970216-chloro-N-(3-chloro-4-methoxyphenyl)-N'-cycloheptyl-[1,3,5]triazine-2,4-diamine

Product 1

HCID 11612454HCID 11612454, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound 133 (1.8 g, 4.70 mmol), potassium carbonate (3.2 g, 23.45 mmol) in dimethylformamide (8 mL) was added 4-hydroxybenzaldehyde (0.69 g, 5.63 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 (1.58 g, 72%). mp 218-220° 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; 265 nm, Rt 25.606 min, 98.06% purity; MS (CI): m/z 468 (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-2944be90e521402cbf50b0891d37e681
Source dataset
uspto-grants-2008_02
Patent number
US07335770B2

Reaction notes

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