Hydrazine → Tert-butyl {2-[4-(5-hydrazino-3-phenyl-1,6-naphthyridin-2-yl)phenyl]-5,8-dioxaspiro[3.4]oct-2-yl}carbamate

HRID 221977

Reaction equation

Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:6]([C:12]1[CH:17]=[CH:16][C:15]([C:18]3([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:21][C:20]4([O:25][CH2:24][CH2:23][O:22]4)[CH2:19]3)=[CH:14][CH:13]=1)=[N:7]2.[NH2:40][NH2:41].C(=O)(O)[O-].[Na+]>O1CCOCC1>[NH:40]([C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:6]([C:12]1[CH:17]=[CH:16][C:15]([C:18]3([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:21][C:20]4([O:25][CH2:24][CH2:23][O:22]4)[CH2:19]3)=[CH:14][CH:13]=1)=[N:7]2)[NH2:41]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of tert-butyl {2-[4-(5-chloro-3-phenyl-1,6-naphthyridin-2-yl)phenyl]-5,8-dioxaspiro[3.4]oct-2-yl}carbamate (1-9) (5 g, 9.2 mmol) in dioxane (100 mL) was added hydrazine (3.0 g, 92 mmol) and the reaction mixture was heated to 100° C. for 1 hour. The reaction mixture was poured into saturated sodium bicarbonate, extracted with chloroform, dried over sodium sulfate, filtered and concentrated to give tert-butyl {2-[4-(5-hydrazino-3-phenyl-1,6-naphthyridin-2-yl)phenyl]-5,8-dioxaspiro[3.4]oct-2-yl}carbamate (1-10) as a yellow solid. MS (M+H)+: 540.

Workup

extractionextracted with chloroform
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-6b0a7464276c417e983619851b8caf32
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207169B2

Linked notes

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