HCID 131728649, compound → HCID 131728648, compound

HRID 1362908Notes

Reaction equation

[C:1]([O:5][C:6](=[O:34])[NH:7][C@@H:8]1[C@@H:13]([C:14]2[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:15]=2[F:22])[CH2:12][CH2:11][N:10]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[C:25]([NH:32][CH3:33])[N:24]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.CO.[Ni]>[C:1]([O:5][C:6](=[O:34])[NH:7][C@@H:8]1[C@@H:13]([C:14]2[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:15]=2[F:22])[CH2:12][CH2:11][N:10]([C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[C:25]([NH:32][CH3:33])[N:24]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirring solution of 68 mg (0.14 mmol) of the product of Step B in 8 mL of 10:1 tetrahydrofuran/methanol under nitrogen was added 0.20 mL Raney Nickel (slurry in water). The resulting mixture under hydrogen was heated at 40° C. for 1 h and then cooled to ambient temperature over 24 h. The mixture was then filtered through a pad of Celite and the filter cake washed with dichloromethane and methanol. The combined filtrate and washings were concentrated in vacuo and the resulting purple solid was purified by reverse phase HPLC (YMC Pro-C18 column, gradient elution, 10-90% acetonitrile/water with 0.1% trifluoroacetic acid) to afford the title compound as a purple crystalline solid. LC/MS 452.5 (M+1).

Workup

temperaturecooled to ambient temperature over 24 h
filtrationThe mixture was then filtered through a pad of Celite
washthe filter cake washed with dichloromethane and methanol
concentrationThe combined filtrate and washings were concentrated in vacuo
customthe resulting purple solid was purified by reverse phase HPLC (YMC Pro-C18 column, gradient elution, 10-90% acetonitrile/water with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-3a0e9fc07e194414b3066de64cf63f01
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884104B2

Reaction notes

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