Azobisisobutyronitrile → HCID 66735524, compound

HRID 1641042Notes

Reaction equation

HRID 1641042 reaction equation
[CH:1]([N:4]([CH:28]([CH3:30])[CH3:29])[C:5](=[O:27])[O:6][C:7]1[C:15]2[C:14]3[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:13]=3[CH2:12][CH2:11][C:10]=2[N:9]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[N:8]=1)([CH3:3])[CH3:2].BrN1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl.Cl.C(O)(C)C>[ClH:20].[CH:28]([N:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:27])[O:6][C:7]1[C:15]2[C:14]3[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:13]=3[CH:12]=[CH:11][C:10]=2[N:9]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[N:8]=1)([CH3:30])[CH3:29]

Participants

7

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 66735206HCID 66735206, compound

Product 1

HCID 66735524HCID 66735524, compoundYield 153.8%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 3776IsopropanolSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

1.65 g (3.38 mmol) of 7-chloro-4,5-dihydro-3-(pyrid-4-yl)-3H-benzo[e]indazol-1-yl N,N-diisopropyl-carbamate, prepared according to the method described in Example 5, 1.105 g (6.21 mmol) of N-bromosuccinimide and 0.127 g (0.78 mmol) of 2,2′-azobis(2-methylpropionitrile) are added to a 100 ml reactor. The mixture, dissolved in 40 ml of carbon tetrachloride, is stirred at reflux for 24 h and is then concentrated under reduced pressure. The resulting product is taken up in 300 ml of dichloromethane and 2 ml of a concentrated aqueous ammonia solution. The organic phase is separated and washed with 200 ml of water and then with 200 ml of a saturated aqueous sodium chloride solution. The organic phase is subsequently dried over magnesium sulphate and then concentrated under reduced pressure. The resulting product is purified by chromatography on an alumina column (eluents: mixture of dichloromethane and of methanol) and then on a silica column (eluents: mixture of dichloromethane and of ethyl acetate). The product thus isolated is converted to the hydrochloride by dissolution in a 0.1N solution of hydrochloric acid in isopropanol. The solution is concentrated to dryness under reduced pressure. After triturating from ethyl ether, filtering off and drying under reduced pressure, 1.2 g (2.6 mmol) of the final product are obtained.

Workup

  1. additionare added to a 100 ml reactor
  2. temperatureat reflux for 24 h
  3. concentrationis then concentrated under reduced pressure
  4. customThe organic phase is separated
  5. washwashed with 200 ml of water
  6. dry with materialThe organic phase is subsequently dried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting product is purified by chromatography on an alumina column (eluents: mixture of dichloromethane and of methanol)
  9. additionon a silica column (eluents: mixture of dichloromethane and of ethyl acetate)
  10. customThe product thus isolated
  11. concentrationThe solution is concentrated to dryness under reduced pressure
  12. customAfter triturating from ethyl ether
  13. filtrationfiltering off

Sources & evidence

ORD record
ord-833c74751d2b4bca82d1e50c6a041da0
Source dataset
uspto-grants-2012_02
Patent number
US08114899B2

Reaction notes

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