Cyanogen Bromide → HCID 9970124, compound

HRID 558264Notes

Reaction equation

HRID 558264 reaction equation
[N:1]#[C:2]Br.[Cl:4][C:5]1[CH:6]=[C:7]([CH:23]=[C:24]([Cl:26])[CH:25]=1)[O:8][C:9]1[C:10]([CH2:21][CH3:22])=[N:11][N:12]([CH2:16][C:17]([NH:19][NH2:20])=[O:18])[C:13]=1[CH2:14][CH3:15]>C(O)C>[Cl:4][C:5]1[CH:6]=[C:7]([CH:23]=[C:24]([Cl:26])[CH:25]=1)[O:8][C:9]1[C:10]([CH2:21][CH3:22])=[N:11][N:12]([CH2:16][C:17]2[O:18][C:2]([NH2:1])=[N:20][N:19]=2)[C:13]=1[CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 10291828HCID 10291828, compound

Product 1

HCID 9970124HCID 9970124, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cyanogen bromide (49 mg, 0.462 mmol) was added to a stirred solution of the hydrazide of Example 11 (150 mg, 0.420 mmol) in ethanol (30 ml), at room temperature, under nitrogen and the resulting solution was heated to reflux for 2.5 hours. After cooling, the mixture was concentrated under reduced pressure to leave a brown oil. The crude product was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:ammonia (98:1.75:0.25, by volume) to provide the title compound (71 mg) as a white powder, m.p. 226-228° C.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux for 2.5 hours
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated under reduced pressure
  5. customto leave a brown oil
  6. customThe crude product was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:ammonia (98:1.75:0.25, by volume)

Sources & evidence

ORD record
ord-85df15c6e86e42c2a8fd5d13eeddc5d2
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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