Ammonia → HCID 66814632, compound

HRID 1097607Notes

Reaction equation

HRID 1097607 reaction equation
Br.[NH2:2][C:3]1[N:4]([CH2:18][C:19]([CH3:22])([OH:21])[CH3:20])[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([Br:15])=[CH:10][C:9]=3[N:8]=[C:7](Cl)[C:6]=2[N:17]=1.[NH3:23]>CO>[NH2:2][C:3]1[N:4]([CH2:18][C:19]([CH3:22])([OH:21])[CH3:20])[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([Br:15])=[CH:10][C:9]=3[N:8]=[C:7]([NH2:23])[C:6]=2[N:17]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 86626306HCID 86626306, compound

Product 1

HCID 66814632HCID 66814632, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
140 °C

Procedure

1-(2-Amino-7-bromo-4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol hydrobromide (1.18 g, 3.19 mmol) and ammonia (50 mL of a 7 N solution in methanol) were added to a pressure vessel, which was sealed and heated at 140° C. for five days. Additional ammonia in methanol was added after two days. When the reaction was complete, the volatiles were removed under reduced pressure, and the residue was stirred with aqueous sodium hydroxide (100 mL of 2 N) for 15 minutes. A solid was present and was isolated by filtration, washed with water and diethyl ether, and dried under vacuum to provide 681 mg of 1-(2,4-diamino-7-bromo-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol as a gray solid.

Workup

  1. customwhich was sealed
  2. customthe volatiles were removed under reduced pressure
  3. customwas isolated by filtration
  4. washwashed with water and diethyl ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-8873dfe905294e11b584af18d970baf9
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

Loading…