Hydrochloric Acid → 6-Methyl-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-amine

HRID 541903Notes

Reaction equation

HRID 541903 reaction equation
Cl.Cl.Cl.[NH2:4][C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][C:13]2[CH:18]=[C:17]([NH:19][C:20]3[C:25]([CH3:26])=[CH:24][N:23]=[C:22](Cl)[N:21]=3)[CH:16]=[CH:15][C:14]=2[NH2:28])[CH:8]=[CH:9][CH:10]=1.Cl.O.[OH-].[Na+]>COCCO.O1CCOCC1>[CH3:26][C:25]1[CH:24]=[N:23][C:22]2[NH:4][C:5]3[CH:10]=[CH:9][CH:8]=[C:7]([CH:6]=3)[CH2:11][CH2:12][C:13]3[CH:18]=[C:17]([NH:19][C:20]=1[N:21]=2)[CH:16]=[CH:15][C:14]=3[NH2:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 866362872-[2-(3-Aminophenyl)ethyl]-N(4)-(2-chloro-5-methylpyrimidin-4-yl)benzene-1,4-diamine Trihydrochloride

Product 1

HCID 579623606-Methyl-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-amineYield 48%

Reagents, catalysts & solvents 2

HCID 80192-MethoxyethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-[2-(3-aminophenyl)ethyl]-N(4)-(2-chloro-5-methylpyrimidin-4-yl)benzene-1,4-diamine trihydrochloride (0.16 g, 0.45 mmol) in 2-methoxyethanol (2 mL) was added 4.0 M of hydrogen chloride in 1,4-dioxane (110 μL). The resultant mixture was heated at 150° C. in the microwave for 15 min. After cooling, water and NaOH (12 N) were added to neutralize the mixture to pH=7. The aqueous layer was extracted with EtOAc four times. The combined organic layers were dried, filtered and concentrated. The residue was purified by silica gel column chromatography to give the desired product as an off-white powder (60 mg, 48%). LCMS for C19H20N5 (M+H)+: m/z=318.2.

Workup

  1. temperatureAfter cooling
  2. extractionThe aqueous layer was extracted with EtOAc four times
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f09dd5814fb240b18709d1864b890720
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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