Cyanogen Bromide → HCID 9970124, compound

HRID 2114628Notes

Reaction equation

HRID 2114628 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-6e2fbb7c2c1349489e828792e936818c
Source dataset
uspto-grants-2008_10
Patent number
US07435728B2

Reaction notes

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