Pyridinium chloride → HCID 86626164, compound

HRID 2383148Notes

Reaction equation

HRID 2383148 reaction equation
Cl.N1C=CC=C[CH:3]=1.[C:8]([O:12][C:13](=[O:39])[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:28]=2)[N:23]=[CH:22][C:21]=1[NH2:38])([CH3:11])([CH3:10])[CH3:9]>C1(C)C=CC=CC=1>[C:8]([O:12][C:13](=[O:39])[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]1[C:20]2[C:29]3[CH:28]=[C:27]([O:30][CH2:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:26]=[CH:25][C:24]=3[N:23]=[CH:22][C:21]=2[N:38]=[CH:3]1)([CH3:11])([CH3:9])[CH3:10]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 86626163HCID 86626163, compound

Product 1

HCID 86626164HCID 86626164, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

For Examples 70-72, the following procedure was used. Under a nitrogen atmosphere, the reagent from the table below (1.5 equivalents) and pyridine hydrochloride (0.01-0.02 equivalents) were added to a solution of tert-butyl{4-[3-amino-6-(benzyloxy)quinolin-4-ylamino]butyl}carbamate (29-36 mmol, 1 equivalent) in toluene (200 mL), and the reaction was heated at reflux for three to five hours. The toluene was removed under reduced pressure. The residue was dissolved in a small amount of toluene, which was removed under reduced pressure. This was repeated three times. The resulting solid was dried under high vacuum at 100° C. to provide the tert-butyl{4-(8-benzyloxy-1H-imidazo[4,5-c]quinolin-1-yl]butyl}carbamate with the substituent indicated in the table below.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for three to five hours
  3. customThe toluene was removed under reduced pressure
  4. dissolutionThe residue was dissolved in a small amount of toluene, which
  5. customwas removed under reduced pressure
  6. customThe resulting solid was dried under high vacuum at 100° C.

Sources & evidence

ORD record
ord-674da7da1da84fb08aea5c958bbc267a
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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