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

HRID 883696

반응식

HRID 883696 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0e288743afcf4e54bf35a04779a5bd29
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236965B2

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