Hydrochloric Acid → HCID 68972619, compound

HRID 2203635Notes

Reaction equation

HRID 2203635 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:24][CH2:25][CH2:26][NH:27]C(=O)OC(C)(C)C)=[CH:5][C:4]=2[N:3]=1.[ClH:35]>>[ClH:35].[ClH:35].[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([CH3:18])([OH:19])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:24][CH2:25][CH2:26][NH2:27])=[CH:5][C:4]=2[N:3]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 58833637HCID 58833637, compound

Product 1

HCID 68972619HCID 68972619, compound

Conditions

Temperature
65 °C

Procedure

tert-Butyl 2-{[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}ethylcarbamate (1.95 g, 4.12 mmol; prepared in Example 562) was slurried in 4.0 M ethanolic hydrogen chloride (15 mL). The reaction was heated at 65° C. for 1.75 hours during which time the starting material dissolved and a precipitate subsequently formed. The reaction mixture was cooled to ambient temperature and the solid was filtered, washed with ethanol, and dried to provide 1.49 g of 1-[4-amino-7-(2-aminoethoxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol dihydrochloride as an off-white powder.

Workup

  1. dissolutiondissolved
  2. customa precipitate subsequently formed
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. filtrationthe solid was filtered
  5. washwashed with ethanol
  6. customdried

Sources & evidence

ORD record
ord-1c37fd4f1b5f460da3516023c5167330
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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