Ammonia → HCID 57550536, compound

HRID 1097594Notes

Reaction equation

[NH2:1][C:2]1[N:3]([CH2:16][C:17]2([OH:21])[CH2:20][CH2:19][CH2:18]2)[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6](Cl)[C:5]=2[N:15]=1.[NH3:22]>CO>[NH2:1][C:2]1[N:3]([CH2:16][C:17]2([OH:21])[CH2:20][CH2:19][CH2:18]2)[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([NH2:22])[C:5]=2[N:15]=1

Participants

Conditions

Temperature: 150 °C

Procedure

1-[(2-Amino-4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)methyl]cyclobutanol (1.14 g, 3.77 mmol) and ammonia (15 mL of a 7 N solution in methanol) were added to a pressure vessel, which was sealed and heated at 150° C. for five days. Additional ammonia in methanol (50 mL) was added after two days. When the reaction was complete, the volatiles were removed under reduced pressure, and the residue was triturated sequentially with methanol and saturated aqueous sodium bicarbonate and isolated by filtration. The resulting yellow solid was purified by automated flash chromatography on silica gel (40+M cartridge, eluting with 0% to 75% CMA in chloroform) followed by recrystallization from methanol. The crystals were dried overnight in a vacuum oven at 90° C. to provide 0.240 g of 1-[(2,4-diamino-1H-imidazo[4,5-c]quinolin-1-yl)methyl]cyclobutanol as pale yellow crystals, mp 295° C. (decomposition).

Workup

customwhich was sealed
customthe volatiles were removed under reduced pressure
customthe residue was triturated sequentially with methanol and saturated aqueous sodium bicarbonate
customisolated by filtration
customThe resulting yellow solid was purified by automated flash chromatography on silica gel (40+M cartridge, eluting with 0% to 75% CMA in chloroform)
customfollowed by recrystallization from methanol
customThe crystals were dried overnight in a vacuum oven at 90° C.

Sources & evidence

ORD record: ord-4b38577c66e744b891b359f9c0e32ae3
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143270B2

Reaction notes

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