Cyanogen Bromide → HCID 86626295, compound

HRID 1097588Notes

Reaction equation

HRID 1097588 reaction equation
[Cl:1][C:2]1[C:11]([NH2:12])=[C:10]([NH:13][C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N:22]#[C:23][Br:24]>C(O)C>[BrH:24].[Cl:1][C:2]1[C:11]2[N:12]=[C:23]([NH2:22])[N:13]([C@@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 10476Cyanogen Bromide2×HCID 86626294HCID 86626294, compound

Product 1

HCID 86626295HCID 86626295, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-chloro-N4-[(1R)-1-phenylethyl]quinoline-3,4-diamine (10.0 g, 33.6 mmol) in ethanol (100 mL) was heated to 80° C. Cyanogen bromide (3.84 g, 36.9 mmol) was added, and the dark solution was heated at 80° C. for two hours. An analysis by LC/MS indicated the presence of starting material. Additional cyanogen bromide (3.84 g, 36.9 mmol) was added, and the reaction was stirred overnight at 80° C. The solvent was removed under reduced pressure, and the resulting oil was stirred with diethyl ether (300 L), isolated by filtration, washed with diethyl ether, and dried under vacuum to provide 13.77 g of 4-chloro-1-[(1R)-1-phenylethyl]-1H-imidazo[4,5-c]quinolin-2-amine hydrobromide as a brown solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. stirringthe resulting oil was stirred with diethyl ether (300 L)
  3. customisolated by filtration
  4. washwashed with diethyl ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-90b8e3ade84841e99415d9d8328d1e07
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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