HCID 86636842, compound → HCID 58001795, compound

HRID 1943178Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:11]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[CH2:10][C:9](=[O:22])[N:8]([CH2:23][C@@H:24]3[CH2:26][O:25]3)[C:7]=2[N:27]=1>CN(C=O)C>[OH:25][CH2:26][C@H:24]1[N:27]2[C:7]3[N:8]([C:9](=[O:22])[CH2:10][N:11]([C:12]([O:14][CH2:15][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[O:13])[C:6]=3[CH:5]=[CH:4][C:3]2=[O:2])[CH2:23]1

Participants

Conditions

Temperature: 120 °C

Procedure

Phenylmethyl 6-(methyloxy)-4-[(2R)-2-oxiranylmethyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine-1(2H)-carboxylate (crude, 15.93 g, estimated 32.8 mmol) was dissolved in DMF (250 ml) at room temperature and heated at 130° C. for 2 nights and at 120° C. for one night. The reaction was complete so DMF was evaporated and the residue treated with water/brine (350/50 ml) and DCM (500 ml). The layers were separated and the aqueous layer was extracted once more with DCM (500 ml). The combined organic extracts were dried on magnesium sulphate, filtered and evaporated to afford a brown oil which was dried under high vacuum over the weekend. The crude product was purified by silica chromatography using a 0-10% methanol/dichloromethane gradient to afford the desired product as a golden foam (3.6 g, 30.9%).

Workup

customwas evaporated
additionthe residue treated with water/brine (350/50 ml) and DCM (500 ml)
customThe layers were separated
extractionthe aqueous layer was extracted once more with DCM (500 ml)
customThe combined organic extracts were dried on magnesium sulphate
filtrationfiltered
customevaporated
customto afford a brown oil which
customwas dried under high vacuum over the weekend
customThe crude product was purified by silica chromatography

Sources & evidence

ORD record: ord-6c05035e921c467087c4b849ace69850
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389524B2

Reaction notes

Loading…