Ethyl orthoformate → HCID 67351503, compound

HRID 1672786Notes

Reaction equation

[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=3)[C:20]([NH:22][NH2:23])=[O:21])[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:27]=1.[CH:28](OCC)(OCC)OCC>>[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:26]=[CH:25][CH:24]=[C:19]([C:20]4[O:21][CH:28]=[N:23][N:22]=4)[CH:18]=3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:27]=1

Participants

Reactant 2

HCID 31214Ethyl orthoformate

HCID 67350136HCID 67350136, compound

Product 1

HCID 67351503HCID 67351503, compoundYield 80%

Conditions

Temperature: 100 °C

Procedure

(S)-3-(9-Methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzoic hydrazide (200 mg, 0.52 mmol) obtained in Step 2 was suspended in triethyl orthoformate (10 mL), and the mixture was stirred at 100° C. for 24 hours. The residue obtained by concentrating the mixture under reduced pressure was then purified by silica gel column chromatography to give (S)-9-methylthio-5-[3-(1,3,4-oxadiazol-2-yl)phenyl]-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (165 mg, 80%).

Workup

customThe residue obtained
concentrationby concentrating the mixture under reduced pressure
customwas then purified by silica gel column chromatography

Sources & evidence

ORD record: ord-a5642c9b3e324ba4a9aec5c3284692c6
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998954B2

Reaction notes

Loading…