Hydrochloric Acid → HCID 68971491, compound

HRID 540930Notes

Reaction equation

HRID 540930 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:22][CH3:23])[N:14]([CH2:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[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]>C(O)C>[ClH:35].[ClH:35].[NH2:27][CH2:26][CH2:25][O:24][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[N:14]([CH2:15][CH:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[C:13]([CH2:22][CH3:23])=[N:12][C:11]=3[C:2]([NH2:1])=[N:3][C:4]=2[CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58833659HCID 58833659, compound

Product 1

HCID 68971491HCID 68971491, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

tert-Butyl 2-{[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}ethylcarbamate (1.8 g, 3.83 mmol) was added to 4.0M ethanolic hydrogen chloride (13 mL) and the reaction was heated to 65° C. for 1 hour. The milky slurry solidified after 20 minutes. Ethanol (10 mL) was added to loosen the solid. After 1 hour, the heat was removed and the reaction was allowed to cool to ambient temperature. Filtration afforded 1.3 g of 7-(2-aminoethoxy)-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydrochloride as a white solid, mp 238° C., decomposition.

Workup

  1. waitAfter 1 hour
  2. customthe heat was removed
  3. temperatureto cool to ambient temperature
  4. filtrationFiltration

Sources & evidence

ORD record
ord-e822a8d6ae894db6979f1ad93656c4af
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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