Boron trifluoride etherate → HCID 90421823, compound

HRID 1752599Notes

Reaction equation

B(F)(F)F.CCOCC.C([SiH](CC)CC)C.[Cl:17][C:18]1[C:23](=[O:24])[N:22]([CH3:25])[CH:21]=[C:20]2[C:26](=[O:42])[N:27]([CH2:30][CH2:31][C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]=3)[CH:28](O)[C:19]=12>C(Cl)Cl>[Cl:17][C:18]1[C:23](=[O:24])[N:22]([CH3:25])[CH:21]=[C:20]2[C:26](=[O:42])[N:27]([CH2:30][CH2:31][C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]=3)[CH2:28][C:19]=12

Participants

Conditions

Temperature: 0 °C

Procedure

BF3.OEt2 (1.234 ml, 9.73 mmol) and triethylsilane (5.18 ml, 32.4 mmol) were added to a suspension of 7-Chloro-5-methyl-2-(2-quinolin-2-yl-ethyl)-1-hydroxyl-1,2-dihydro-5H-pyrrolo[3,4-c]pyridine-3,6-dione (1.2 g, 3.24 mmol, see Example c3.1)) in DCM (5 ml) at 0° C. and the reaction stirred at 0° C. for 3 h, which was then warmed to r.t. and stirred overnight. The solvent was removed and the resulting mixture was purified via preparative HPLC (Waters 2767 PHW003, eluent: MeCN/aqueous 0.05% solution of ammonium hydrogen carbonate (gradient: 20:80 to 40:60 over 14 min), column: Hanbon Benetnach C18, 10 μm, 20×250 mm) to afford the title compound (65 mg, 6.5% yield).

Workup

customat 0° C.
temperaturewhich was then warmed to r.t.
stirringstirred overnight
customThe solvent was removed
customthe resulting mixture was purified via preparative HPLC (Waters 2767 PHW003, eluent: MeCN/aqueous 0.05% solution of ammonium hydrogen carbonate (gradient: 20:80 to 40:60 over 14 min), column: Hanbon Benetnach C18, 10 μm, 20×250 mm)

Sources & evidence

ORD record: ord-4a6a838c358d4054a17bdf5dd1e7e61f
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163019B2

Reaction notes

Loading…