HCID 22055255, compound → HCID 22055263, compound

HRID 1829923Notes

Reaction equation

[Cl:1][C:2]1[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[CH:16][C:3]=1[O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1>CC(O)=O.CCOC(C)=O.[Fe]>[Cl:1][C:2]1[CH:19]=[C:18]([NH2:20])[CH:17]=[CH:16][C:3]=1[O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 12A (95.5 mg, 0.30 mmol) and Fe powder (135 mg, 2.4 mmol) in HOAc/EtOAc (1/1) (2 ml) was heated at 70° C. for 3.5 h. The mixture was cooled to rt, filtered through an 1″ celite pad and rinsed with HOAc/EtOAc (1/1) (4×8 ml). The filtrate was concentrated in vacuo. The residue was diluted with 1N NaOH (40 ml), extracted with EtOAc (2×60 ml) and the combined EtOAc extracts were washed with brine (1×20 ml), dried (MgSO4), filtered and concentrated in vacuo to give 12B (83.1 mg, 79% pure) which was used in next step without further purification. Analytical HPLC retention time=2.08 min. (YMC Xterra S7 C18, 3.0×50 mm column, 10–90% aqueous methanol over 2 minutes containing 0.1% TFA, 5 mL/min, monitoring at 220 nm).

Workup

temperatureThe mixture was cooled to rt
filtrationfiltered through an 1″ celite pad
washrinsed with HOAc/EtOAc (1/1) (4×8 ml)
concentrationThe filtrate was concentrated in vacuo
additionThe residue was diluted with 1N NaOH (40 ml)
extractionextracted with EtOAc (2×60 ml)
washthe combined EtOAc extracts were washed with brine (1×20 ml)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5684564694674610a2f607a4dbcdb6b4
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07064203B2

Reaction notes

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