Cyanogen Bromide → HCID 86626306, compound

HRID 1097606Notes

Reaction equation

HRID 1097606 reaction equation
[NH2:1][C:2]1[C:3]([Cl:19])=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])=[CH:9][CH:8]=[C:7]([Br:18])[CH:6]=2.[N:20]#[C:21]Br>C(O)C>[BrH:18].[NH2:20][C:21]1[N:12]([CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])[C:11]2[C:10]3[CH:9]=[CH:8][C:7]([Br:18])=[CH:6][C:5]=3[N:4]=[C:3]([Cl:19])[C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 86626305HCID 86626305, compound

Product 1

HCID 86626306HCID 86626306, compoundYield 136.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 1-[(3-amino-7-bromo-2-chloroquinolin-4-yl)amino]-2-methylpropan-2-ol (1.5 g, 4.35 mmol) in ethanol (25 mL) was heated to 80° C. Cyanogen bromide (0.50 g, 4.8 mmol) was added to the resulting solution, and the reaction was heated at 80° C. overnight and allowed to cool. A precipitate was present and was isolated by filtration, washed with diethyl ether, and dried under vacuum for one hour to provide 1.34 g of 1-(2-amino-7-bromo-4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol hydrobromide as a pinkish-white solid, mp >260° C.

Workup

  1. temperaturethe reaction was heated at 80° C. overnight
  2. temperatureto cool
  3. customwas isolated by filtration
  4. washwashed with diethyl ether
  5. customdried under vacuum for one hour

Sources & evidence

ORD record
ord-158c9454a670476789a4e81a29cc0a64
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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