Hydrochloric Acid → 4-[(diisobutylamino)methyl]-N-(3-{methyl[2-(4-pyridinyl)ethyl]amino}propyl)-1,2-benzenediamine

HRID 883696

Reaction equation

HRID 883696 reaction equation
[CH2:1]([N:5]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:6](=O)[C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH2:14][CH2:15][CH2:16][N:17]([CH3:26])[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[C:9]([N+:27]([O-])=O)[CH:8]=1)[CH:2]([CH3:4])[CH3:3].Cl.C(OCC)(=O)C>O1CCCC1>[CH2:1]([N:5]([CH2:6][C:7]1[CH:8]=[C:9]([NH2:27])[C:10]([NH:13][CH2:14][CH2:15][CH2:16][N:17]([CH3:26])[CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=2)=[CH:11][CH:12]=1)[CH2:31][CH:32]([CH3:34])[CH3:33])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 69026668HCID 69026668, compound

Product 1

HCID 690281664-[(diisobutylamino)methyl]-N-(3-{methyl[2-(4-pyridinyl)ethyl]amino}propyl)-1,2-benzenediamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A molar solution of borane-tetrahydrofuran complex (6.25 ml, 15 eq) is added dropwise to a solution of N,N-diisobutyl-4-({3-[methyl(2-pyridin-4-ylethyl)amino]propyl}amino)-3-nitrobenzamide (200 mg, 1 eq) in tetrahydrofuran (3 ml) cooled down to 0° C. The mixture is heated under reflux for 20 hours then cooled down to 0° C. and hydrolysed with a 6N aqueous solution of hydrochloric acid (12 ml). After 1 hour 30 minutes under reflux, the mixture is cooled down to 0° C. and brought to basic pH by a 6N aqueous solution of soda. After adding ethyl acetate, decanting and extracting, the organic phases are combined, followed by washing with salt water, drying over sodium sulphate and evaporating under reduced pressure. Purification by flash chromatography on silica gel (eluent: 100% dichloromethane to dichloromethane/methanol 8:2) produces the expected compound in the form of an oil (92 mg, 51% yield).

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 20 hours
  3. temperatureAfter 1 hour 30 minutes under reflux
  4. temperaturethe mixture is cooled down to 0° C.
  5. customdecanting
  6. extractionextracting
  7. washby washing with salt water
  8. dry with materialdrying over sodium sulphate
  9. customevaporating under reduced pressure
  10. customPurification by flash chromatography on silica gel (eluent: 100% dichloromethane to dichloromethane/methanol 8:2)

Sources & evidence

ORD record
ord-0e288743afcf4e54bf35a04779a5bd29
Source dataset
uspto-grants-2012_08
Patent number
US08236965B2

Linked notes

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