HCID 69081100, compound → HCID 57657250, compound

HRID 244874Notes

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]([CH:24]=[CH:25][C:26]#[N:27])=[CH:5][C:4]=2[N:3]=1>[Pd].CO>[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]([CH2:24][CH2:25][C:26]#[N:27])=[CH:5][C:4]=2[N:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A glass Parr vessel was charged with 10% palladium on carbon (0.05 g), methanol (20 mL), and 3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enenitrile (100 mg, 0.27 mmol). The vessel was evacuated and charged with hydrogen gas (40 psi, 2.8×105 Pa). The reaction was shaken at 50° C. for approximately 18 hours and then cooled to ambient temperature. The reaction mixture was sequentially filtered, concentrated under reduced pressure, and purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a CMA:chloroform gradient, 0-30% CMA). A final recrystallization from acetonitrile provided 71 mg of 3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanenitrile as a white solid, mp 273-275° C.

Workup

customThe vessel was evacuated
additioncharged with hydrogen gas (40 psi, 2.8×105 Pa)
temperaturecooled to ambient temperature
filtrationThe reaction mixture was sequentially filtered
concentrationconcentrated under reduced pressure
custompurified by chromatography
washeluting with a CMA
customA final recrystallization from acetonitrile

Sources & evidence

ORD record: ord-dfaf962df1ab44db80af303a2cd060bd
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658666B2

Reaction notes

Loading…