Hydrochloric Acid → HCID 68972937, compound

HRID 540886Notes

Reaction equation

HRID 540886 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:23][O:24][CH2:25][CH3:26])[N:14]([CH2:15][CH:16]3[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]3)[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:27][CH2:28][CH2:29][NH:30]C(=O)OC(C)(C)C)=[CH:5][C:4]=2[N:3]=1.[ClH:38]>C(O)C>[ClH:38].[ClH:38].[NH2:30][CH2:29][CH2:28][O:27][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[N:14]([CH2:15][CH:16]4[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]4)[C:13]([CH2:23][O:24][CH2:25][CH3:26])=[N:12][C:11]=3[C:2]([NH2:1])=[N:3][C:4]=2[CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58833616HCID 58833616, compound

Product 1

HCID 68972937HCID 68972937, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A suspension of tert-butyl 2-{[4-amino-1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}ethylcarbamate (prepared in Example 372, 1.5 g, 2.9 mmol) in ethanol (20 mL) and 4.3 M HCl in ethanol (2.70 mL, 17.5 mmol) was heated at reflux overnight. The reaction mixture was allowed to cool to room temperature and a white solid was collected by filtration, washed with ethanol, and dried under vacuum at 60° C. to yield 0.85 g of 7-(2-aminoethoxy)-1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydrochloride as a white solid, mp 221-223° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. filtrationa white solid was collected by filtration
  4. washwashed with ethanol
  5. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-e647a4c1d5dc4a60b5c5aaa19d55d1a6
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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