Hydrochloric Acid → HCID 67051023, compound

HRID 598281Notes

Reaction equation

HRID 598281 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[N:13]=[C:14]([CH2:25][CH2:26][CH2:27][CH2:28][NH:29]C(=O)OC(C)(C)C)[N:15]([CH2:16][CH2:17][O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]=2[C:10]2[CH:9]=[CH:8][C:7]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[CH:6][C:5]=2[N:4]=1>C(O)C>[NH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C:14]1[N:15]([CH2:16][CH2:17][O:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:11]2[C:10]3[CH:9]=[CH:8][C:7]([O:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[CH:6][C:5]=3[N:4]=[C:3]([NH2:2])[C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86626158HCID 86626158, compound

Product 1

HCID 67051023HCID 67051023, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of hydrochloric acid (5 mL of 1.5 M in ethanol) was added to a mixture of tert-butyl {4-[4-amino-7-benzyloxy-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-2-yl]butyl}carbamate (823 mg, 1.41 mmol) and ethanol. The reaction was heated at reflux for 30 minutes and became homogeneous. The solvent was removed under reduced pressure. The residue was recrystallized from methanol, isolated by filtration, washed with diethyl ether, and dried under reduced pressure to provide 534 mg of 2-(4-aminobutyl)-7-benzyloxy-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine as yellow crystals.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 30 minutes
  3. customThe solvent was removed under reduced pressure
  4. customThe residue was recrystallized from methanol
  5. customisolated by filtration
  6. washwashed with diethyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-9999200f7d6849a5a5208854e11aed1b
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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