Hydrochloric Acid → HCID 57961661, compound

HRID 541877Notes

Reaction equation

HRID 541877 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]2[C:19]([Cl:20])=[CH:18][N:17]=[C:16](Cl)[N:15]=2)[CH:8]=1.Cl.O.[OH-].[Na+]>COCCO.O1CCOCC1>[Cl:20][C:19]1[CH:18]=[N:17][C:16]2[NH:1][C:2]3[CH:24]=[CH:23][CH:22]=[C:4]([CH:3]=3)[CH2:5][NH:6][C:7]3[CH:8]=[C:9]([NH:13][C:14]=1[N:15]=2)[CH:10]=[CH:11][CH:12]=3

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 57962617HCID 57962617, compound

Product 1

HCID 57961661HCID 57961661, compoundYield 10.2%

Reagents, catalysts & solvents 2

HCID 80192-MethoxyethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-(3-aminobenzyl)-N′-(2,5-dichloropyrimidin-4-yl)benzene-1,3-diamine (900 mg, 2.0 mmol) in 2-methoxyethanol (18 mL) was added 4.00 M of hydrogen chloride in 1,4-dioxane (1.88 mL). The resultant mixture was heated at 150° C. in the microwave for 5 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 (66 mg, 8%). LCMS for C17H15ClN5 (M+H)+: m/z=324.0.

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-973e0433f1474049b0f66f983aa63d05
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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