Ethyl Acetate → Tert-butyl {1-[4-(5-hydrazino-3-phenyl-1,6-naphthyridin-2-yl)phenyl]cyclobutyl}carbamate

HRID 2064441Notes

Reaction equation

[NH2:1][NH2:2].Cl[C:4]1[N:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:8]([C:14]1[CH:19]=[CH:18][C:17]([C:20]3([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:23][CH2:22][CH2:21]3)=[CH:16][CH:15]=1)=[N:9]2.C(OCC)(=O)C>O1CCOCC1>[NH:1]([C:4]1[N:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:8]([C:14]1[CH:19]=[CH:18][C:17]([C:20]3([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:23][CH2:22][CH2:21]3)=[CH:16][CH:15]=1)=[N:9]2)[NH2:2]

Participants

Conditions

Temperature: 95 °C

Procedure

Anhydrous hydrazine (25 mL, 797 mmol) was added to a stirred solution of chloronaphthyridine (1-5) (25.12 g, 51.7 mmol) in 1,4-dioxane (200 mL) under an atmosphere of nitrogen and the reaction mixture was heated to 95° C. After 30 min the solution was cooled to room temperature, ethyl acetate (400 mL) was added and the solution was washed with a saturated solution of sodium bicarbonate, followed by water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give (1-6) as an orange solid.

Workup

temperatureAfter 30 min the solution was cooled to room temperature
washthe solution was washed with a saturated solution of sodium bicarbonate
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9307d33fbc27495b8089d4bb65246d92
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288407B2

Reaction notes

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