Sodium Hydroxide → HCID 11236549, compound

HRID 1374033Notes

Reaction equation

HRID 1374033 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][C@H:3]1[CH2:4][OH:5].[OH-].[Na+].Cl[C:12]1[N:17]=[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([Cl:27])[CH:20]=2)[N:15]=[C:14]([NH:28][CH:29]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[N:13]=1>C1C=CC=CC=1>[Cl:27][C:21]1[CH:20]=[C:19]([NH:18][C:16]2[N:15]=[C:14]([NH:28][CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]3)[N:13]=[C:12]([O:5][CH2:4][CH:3]3[CH2:6][CH2:7][CH2:8][N:2]3[CH3:1])[N:17]=2)[CH:24]=[CH:23][C:22]=1[O:25][CH3:26]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 643492(2S)-1-Methyl-2-pyrrolidinemethanolHCID 218970216-chloro-N-(3-chloro-4-methoxyphenyl)-N'-cycloheptyl-[1,3,5]triazine-2,4-diamine

Product 1

HCID 11236549HCID 11236549, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of N-methyl prolinol (0.226 g, 1.96 mmol) and sodium hydroxide (79 mg, 1.96 mmol) in benzene (10 mL) was heated to reflux for 2 hours with stirring under nitrogen atmosphere and then cooled to 25° C. followed by the addition of compound 133 (0.25 g, 0.65 mmol) at same temperature. The mixture was heated to reflux for 6 hours, concentrated under vacuum and diluted with water (3 mL). The gum which separated was collected (by decanting out the liquid portion) and purified by column chromatography (1–3% MeOH—CHCl3) to afford the title compound E25 as a semi-solid (0.06 g, 20%). HPLC: Symmetry shield RP18 (250×4.6 mm) 5 microns [solvent A=0.01 M KH2PO4 (pH 3.0); solvent B=CH3CN], Gradient elution program: T/% B=0/35, 10/35, 40/80, 50/80, 55/35, 60/35; 270 nm, Rt 15.51 min, 99.55% purity; MS (CI): m/z 461 (M+H, 100).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe mixture was heated
  4. temperatureto reflux for 6 hours
  5. concentrationconcentrated under vacuum
  6. additiondiluted with water (3 mL)
  7. customThe gum which separated
  8. customwas collected (
  9. customby decanting out the liquid portion) and
  10. custompurified by column chromatography (1–3% MeOH—CHCl3)

Sources & evidence

ORD record
ord-6a3fc39dc4b649e48943cdcd00a0edbe
Source dataset
uspto-grants-2007_01
Patent number
US07163943B2

Reaction notes

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