Water → HCID 21057796, compound

HRID 1375513Notes

Reaction equation

HRID 1375513 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.[OH-].[Na+].O.Cl[C:11]1[N:16]=[C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([Cl:26])[CH:19]=2)[N:14]=[C:13]([NH:27][CH:28]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[N:12]=1>O1CCOCC1>[Cl:26][C:20]1[CH:19]=[C:18]([NH:17][C:15]2[N:14]=[C:13]([NH:27][CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)[N:12]=[C:11]([N:1]3[CH2:6][CH2:5][S:4][CH2:3][CH2:2]3)[N:16]=2)[CH:23]=[CH:22][C:21]=1[O:24][CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 67164ThiomorpholineHCID 218970216-chloro-N-(3-chloro-4-methoxyphenyl)-N'-cycloheptyl-[1,3,5]triazine-2,4-diamine

Product 1

HCID 21057796HCID 21057796, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of thiomorpholine (97 mg, 0.942 mmol), sodium hydroxide (31.4 mg, 0.785 mmol) and water (0.5 mL) in 1,4-dioxane (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 Na2SO4 and concentrated under vacuum. The residue thus obtained was purified by column chromatography (10–20% EtOAc-Hexane) to afford the title compound E27 as a pale yellow solid (0.26 g, 74%). mp 78–80° C.; HPLC: Inertsil ODS 3V (250×4.6 mm) 5 microns [solvent A=0.01 M KH2PO4; solvent B=CH3CN], A:B=20:80; 220 nm, Rt 20.36 min, 97.15% purity; MS (CI): m/z 449 (M+H, 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 Na2SO4
  10. concentrationconcentrated under vacuum
  11. customThe residue thus obtained
  12. customwas purified by column chromatography (10–20% EtOAc-Hexane)

Sources & evidence

ORD record
ord-e98cb9cae4134bc9a8c64b91b39105da
Source dataset
uspto-grants-2007_01
Patent number
US07169785B2

Reaction notes

Loading…