Benzene → HCID 90384693, compound

HRID 1846410Notes

Reaction equation

[CH2:1]([NH:8][C:9]([C@H:11]1[CH2:20][C:19]23[CH2:21][CH2:22][C@:12]1([OH:47])[CH:13]1[O:30][C:28]4=[C:29]5[C@@:14]12[CH2:15][CH2:16][N:17]([CH2:43][CH:44]1[CH2:46][CH2:45]1)[C@@H:18]3[CH2:23][C:24]5=[CH:25][CH:26]=[C:27]4OC1N(C2C=CC=CC=2)N=NN=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC=CC=1.O.NN>C(O)C.C(OCC)(=O)C.[C].[Pd]>[CH2:1]([NH:8][C:9]([C@H:11]1[CH2:20][C:19]23[CH2:21][CH2:22][C@:12]1([OH:47])[CH:13]1[O:30][C:28]4=[C:29]5[C@@:14]12[CH2:15][CH2:16][N:17]([CH2:43][CH:44]1[CH2:45][CH2:46]1)[C@@H:18]3[CH2:23][C:24]5=[CH:25][CH:26]=[CH:27]4)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

Under an argon atmosphere, the compound 112 (2.33 g, 3.69 mmol) was dissolved in ethanol (20 mL), benzene (36 mL), and water (10 mL), the solution was added with 10% palladium-carbon (2.3 g), and aqueous hydrazine (64 v/v %, 25 mL), and the mixture was stirred at 85° C. for 16 hours. The reaction mixture was diluted with ethyl acetate, and filtered through Celite. The organic layer was washed with water, and saturated brine, dried over anhydrous sodium sulfate, and then concentrated. The obtained crude product was purified by silica gel column chromatography to give the title compound 113 (650 mg, 37%).

Workup

filtrationfiltered through Celite
washThe organic layer was washed with water, and saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated
customThe obtained crude product
customwas purified by silica gel column chromatography

Sources & evidence

ORD record: ord-a820cf129ee54f7b92b06cd539a88618
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952030B2

Reaction notes

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