Hydrochloric Acid → 4-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}piperidin-4-ol dihydrochloride

HRID 44701Notes

Reaction equation

[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:30][O:31][CH2:32][CH3:33])[N:14]([CH2:15][C:16]3([OH:29])[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[ClH:34]>C(O)C>[ClH:34].[ClH:34].[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:30][O:31][CH2:32][CH3:33])[N:14]([CH2:15][C:16]3([OH:29])[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of tert-butyl 4-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}-4-hydroxypiperidine-1-carboxylate (0.720 g, 1.62 mmol, prepared as described in Example 4) in ethanol (10 mL) was added 4.3 M HCl in ethanol (2 mL). The solution was heated at 65° C. for 1.5 h. After the mixture cooled to rt, a solid was isolated by filtration. The solid was washed with diethyl ether and dried under reduced pressure at 100° C. to afford 4-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}piperidin-4-ol dihydrochloride as a 0.5 hydrate and as a white solid, mp>260° C. MS (APCI) m/z 356 (M+H)+; Anal. calcd for C19H25N5O2.2HCl.0.5 H20: C, 52.18; H, 6.45; N, 16.01. Found: C, 52.32; H, 6.40; N, 15.90.

Workup

temperatureAfter the mixture cooled to rt
customa solid was isolated by filtration
washThe solid was washed with diethyl ether
customdried under reduced pressure at 100° C.

Sources & evidence

ORD record: ord-ff227f31191840b4a6e2c85bfc586881
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541438B2

Reaction notes

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