Sodium Hydroxide → HCID 86594680, compound

HRID 916129Notes

Reaction equation

HRID 916129 reaction equation
[CH3:1][C:2]1N=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][CH:3]=1.[OH-:10].[Na+].Cl[C:13]1[N:18]=[C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([Cl:28])[CH:21]=2)[N:16]=[C:15]([NH:29][CH:30]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[N:14]=1>C1C=CC=CC=1>[Cl:28][C:22]1[CH:21]=[C:20]([NH:19][C:17]2[N:16]=[C:15]([NH:29][CH:30]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[N:14]=[C:13]([O:9][CH2:8][CH:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[O:10]3)[N:18]=2)[CH:25]=[CH:24][C:23]=1[O:26][CH3:27]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 707366-Methyl-2-pyridylmethanolHCID 218970216-chloro-N-(3-chloro-4-methoxyphenyl)-N'-cycloheptyl-[1,3,5]triazine-2,4-diamine

Product 1

HCID 86594680HCID 86594680, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 6-methyl-2-pyridylmethanol (145 mg, 1.17 mmol) and sodium hydroxide (63 mg, 1.57 mmol) in benzene (15 mL) was heated to reflux for 3 hours with stirring under nitrogen atmosphere and then cooled to 25° C. followed by the addition of compound 133 (0.30 g, 0.785 mmol) at same temperature. The mixture was heated to reflux for 12 hours, concentrated under vacuum and diluted with water (20 mL). The mixture was then 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 (70-80% EtOAc-Hexane) to afford the title compound E30 as a hygroscopic solid (257 mg, 70%). 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 23.93 min, 99.14% purity; MS (CI): m/z 469 (M+, 100).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. temperatureThe mixture was heated
  4. temperatureto reflux for 12 hours
  5. concentrationconcentrated under vacuum
  6. additiondiluted with water (20 mL)
  7. extractionThe mixture was then extracted with EtOAc (2×20 mL)
  8. washThe combined organic layers were washed with water (2×10 mL)
  9. dry with materialdried over anhydrous sodium sulphate
  10. concentrationconcentrated under vacuum
  11. customThe residue thus obtained
  12. customwas purified by column chromatography (70-80% EtOAc-Hexane)

Sources & evidence

ORD record
ord-6e30d3d93963405e8b6a1f73d05cd13a
Source dataset
uspto-grants-2007_09
Patent number
US07268134B2

Reaction notes

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