Hydrochloric Acid → 3-(Pyridin-4-yl)-5-(2-(quinolin-2-yl)ethyl)furo[3,2-c]pyridin-4(5H)-one

HRID 920941Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[N:34]1[CH:39]=[CH:38][C:37]([C:40]2[C:44]3[C:45](=[O:49])[NH:46][CH:47]=[CH:48][C:43]=3[O:42][CH:41]=2)=[CH:36][CH:35]=1.[N:50]1[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[CH:53]=[CH:52][C:51]=1[CH2:60][CH2:61]O.Cl>C1COCC1.CC(=O)OCC>[N:34]1[CH:35]=[CH:36][C:37]([C:40]2[C:44]3[C:45](=[O:49])[N:46]([CH2:61][CH2:60][C:51]4[CH:52]=[CH:53][C:54]5[C:59](=[CH:58][CH:57]=[CH:56][CH:55]=5)[N:50]=4)[CH:47]=[CH:48][C:43]=3[O:42][CH:41]=2)=[CH:38][CH:39]=1

Participants

Conditions

Temperature: 15 °C

Procedure

To a solution of triphenylphosphine (247 mg, 0.942 mmol) in THF (10 mL), DIAD (0.321 mL, 1.65 mmol) was added. The mixture was cooled to 15° C. 3-(Pyridin-4-yl)furo[3,2-c]pyridin-4(5H)-one (100 mg, 0.471 mmol) and 2-(quinolin-2-yl)ethanol from example from example a1 were added. After stirring overnight at room temperature, EA and 2M HCl were added. The phases were separated and extracted with EA. The organic phase was washed with water. The acidic aqueous phase was basified with 2M NaOH and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography to give 69 mg of the title compound (36.3%) as hydrochloride salt as dark yellow solid.

Workup

customThe phases were separated
extractionextracted with EA
washThe organic phase was washed with water
extractionextracted with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-4d092cf5421746948d7091afacfa9724
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273068B2

Reaction notes

Loading…