Sodium Hydroxide → HCID 21897105, compound

HRID 916124Notes

Reaction equation

HRID 916124 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.[OH-].[Na+].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>C1C=CC=CC=1>[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:4]3[CH2:5][CH2:6][CH2:7][CH:2]([OH:1])[CH2:3]3)[N:16]=2)[CH:23]=[CH:22][C:21]=1[O:24][CH3:25]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 232933-HydroxypiperidineHCID 218970216-chloro-N-(3-chloro-4-methoxyphenyl)-N'-cycloheptyl-[1,3,5]triazine-2,4-diamine

Product 1

HCID 21897105HCID 21897105, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 3-hydroxypiperidine (0.198 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 (10 mL). The precipitated solid was filtered off and purified by column chromatography (1-2% MeOH-CHCl3) to afford the title compound E23 as an off-white solid (0.06 g, 21%). mp 100-102° C.; HPLC: Hichrom RPB (250×4.6 mm) 5 microns [solvent A=0.01 M KH2PO4 (pH 5.5); solvent B=CH3CN], Gradient elution program: T/%B=0/20, 10/20,25/80, 40/80, 55/60, 65/20, 70/20; 270 nm, Rt 41.95 min, 98.43% purity; MS (CI): m/z 447 (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 (10 mL)
  7. filtrationThe precipitated solid was filtered off
  8. custompurified by column chromatography (1-2% MeOH-CHCl3)

Sources & evidence

ORD record
ord-9915ab410a9e4ae3909894d3400ad8b3
Source dataset
uspto-grants-2007_09
Patent number
US07268134B2

Reaction notes

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