HCID 178461354, compound → HCID 178461353, compound

HRID 2302069Notes

Reaction equation

HRID 2302069 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14]3[C:19]([C:20]=2Cl)=[CH:18][CH:17]=[C:16]([C:22]([F:25])([F:24])[F:23])[CH:15]=3)=[O:10])[CH2:4][CH2:3]1>[Pd].O1CCCC1.ClCCl>[CH3:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[C:16]([C:22]([F:25])([F:23])[F:24])[CH:15]=3)=[O:10])[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 178461354HCID 178461354, compound

Product 1

HCID 178461353HCID 178461353, compoundYield 17.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

The amide (253 mg, 0.68 mmol) in 3:1 tetrahydrofuran-dichloromethane (75 mL) containing 10% Pd on carbon (150 mg) was hydrogenated at 40 p.s.i. H2 for 10 min (ambient temperature). Filtration of the reaction mixture and chromatography through a Biotage silica cartridge (8×4 cm i.d.) using a gradient of hexane to 20% ethyl acetate (in hexane) afforded 40 mg (12%) of 431:

Workup

  1. filtrationFiltration of the reaction mixture and chromatography through a Biotage silica cartridge (8×4 cm i.d.)

Sources & evidence

ORD record
ord-17fa393a42c64d5482e138a52de57668
Source dataset
uspto-grants-2002_08
Patent number
US06429207B1

Reaction notes

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