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

HRID 2104122Notes

Reaction equation

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

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-acf3e5ac2b174e298e5bcf07dd10b32c
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576209B2

Reaction notes

Loading…