Cyclopentanone → HCID 52917034, compound

HRID 1020168Notes

Reaction equation

[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16]1(=O)[CH2:20][CH2:19][CH2:18][CH2:17]1.B.N1C=CC=CC=1C>CO.CC(O)=O>[CH:16]1([NH:15][C:12]2[CH:11]=[CH:10][C:9]([C:8]#[C:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:14][N:13]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

Conditions

Temperature: 40 °C

Procedure

5-Phenylethynyl-pyridin-2-ylamine (100 mg, 0.515 mmol), cyclopentanone (77 mg, 0.927 mmol) and 2-picoline borane (85 mg, 0.927 mmol) were dissolved in 5.5 ml MeOH:AcOH (10:1 v/v) and stirred for 48 hours at 40° C. MeOH was then evaporated and the residue was acidified to pH 1 with 6 ml 10% HCl. The resulting white suspension was stirred for 2 hours. The mixture was extracted with dichloromethane and brine. The pH of the aqueous layer was adjusted to 12 by addition of conc. NaOH and the mixture was extracted twice with dichloromethane. The organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silicagel (heptane/ethyl acetate 100:0→50:50 gradient). The desired compound was obtained as a light yellow solid (70 mg, 53%), MS: m/e=263.3 (M+H+).

Workup

customMeOH was then evaporated
stirringThe resulting white suspension was stirred for 2 hours
extractionThe mixture was extracted with dichloromethane and brine
additionThe pH of the aqueous layer was adjusted to 12 by addition of conc. NaOH
extractionthe mixture was extracted twice with dichloromethane
dry with materialThe organic extracts were dried with sodium sulfate
filtrationfiltered
customevaporated
customThe crude product was purified by flash chromatography on silicagel (heptane/ethyl acetate 100:0→50:50 gradient)

Sources & evidence

ORD record: ord-d7c28bb2403c4c27b6bcd03ff776bb1a
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716316B2

Reaction notes

Loading…