Triphenylphosphine → ethyl 5-{4-[2-(11-ethyl-6,11-dihydro-5-methyl-6-oxo-5H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-8-yl)ethoxy]phenyl}-2-methyl-3-furanecarboxylate

HRID 393279Notes

Reaction equation

CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH2:15]([N:17]1[C:23]2[N:24]=[CH:25][C:26]([CH2:28][CH2:29][OH:30])=[CH:27][C:22]=2[C:21](=[O:31])[N:20]([CH3:32])[C:19]2[CH:33]=[CH:34][CH:35]=[N:36][C:18]1=2)[CH3:16].O[C:38]1[CH:43]=[CH:42][C:41]([C:44]2[O:48][C:47]([CH3:49])=[C:46]([C:50]([O:52][CH2:53][CH3:54])=[O:51])[CH:45]=2)=[CH:40][CH:39]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[CH2:15]([N:17]1[C:23]2[N:24]=[CH:25][C:26]([CH2:28][CH2:29][O:30][C:38]3[CH:39]=[CH:40][C:41]([C:44]4[O:48][C:47]([CH3:49])=[C:46]([C:50]([O:52][CH2:53][CH3:54])=[O:51])[CH:45]=4)=[CH:42][CH:43]=3)=[CH:27][C:22]=2[C:21](=[O:31])[N:20]([CH3:32])[C:19]2[CH:33]=[CH:34][CH:35]=[N:36][C:18]1=2)[CH3:16]

Participants

Conditions

Temperature: 25 °C

Procedure

DIAD (60 μL, 0.31 mmol) was added dropwise to a solution of 11-ethyl-5,11-dihydro-8-(2-hydroxyethyl)-5-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (75.8 mg, 0.25 mmol), ethyl 5-(4-hydroxyphenyl)-2-methyl-3-furanecarboxylate (75 mg, 0.30 mmol) and PPh3 (80.0 mg, 0.30 mmol) in THF (3 mL) at 25° C. The reaction mixture was stirred at 25° C. for 48 h. The mixture was concentrated under reduced pressure. The residue was purified by flash chromatography (Hexane:EtOAc, 3:2) to give the title compound (64 mg, 48% yield) as yellow oil.

Workup

concentrationThe mixture was concentrated under reduced pressure
customThe residue was purified by flash chromatography (Hexane:EtOAc, 3:2)

Sources & evidence

ORD record: ord-6f6e163c957d42e781fc7f9f6833de3c
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06806265B2

Reaction notes

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