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

HRID 1727423

反応式

HRID 1727423 の反応式
[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]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 69026668HCID 69026668、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a061309e876445ca8bdcb9ef592ff9cf
出典データセット
uspto-grants-2009_02
特許番号
US07495110B2

関連ノート

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