Hydrazine → 1-(2-Aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364331Notes

Reaction equation

O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:22]=2)[C:17]([OH:32])=[C:16]([C:33]([NH:35][CH2:36][CH2:37][OH:38])=[O:34])[C:15]1=[O:39].NN>CCO>[NH2:3][CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[CH:22]=2)[C:17]([OH:32])=[C:16]([C:33]([NH:35][CH2:36][CH2:37][OH:38])=[O:34])[C:15]1=[O:39]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (0.255 g, 0.48 mmol) in EtOH (80 mL) under nitrogen was treated with hydrazine (0.151 mL, 4.81 mmol) for 1 h@50° C. Additional hydrazine was added (0.075 mL @1 h) after 1 and 4 hours (0.15 mL @ 4 h) and the reaction was stirred for a total of 8 h@50° C. The reaction was then capped and cooled in a refrigerator overnight. The resulting suspension was filtered then thoroughly dried under high vacuum to provide the title compound as an off-white solid: 1H NMR (300 MHz, DMSO-D6) δ ppm 2.8 (m, 1 H), 3.4 (m, 2 H), 3.6 (m, 2 H), 4.1 (s, 2 H), 4.2 (m, 2 H), 4.9 (bs, 1 H), 7.1 (t, J=8.7 Hz, 2 H), 7.4 (m, 2 H), 8.1 (s, 1 H), 8.5 (s, 1 H), 10.5 (m, 1 H); ES+ MS: 401 (M+H+).

Workup

customThe reaction was then capped
temperaturecooled in a refrigerator overnight
filtrationThe resulting suspension was filtered
customthen thoroughly dried under high vacuum

Sources & evidence

ORD record: ord-3e677eb686c64eb9a3d54ec072afdd38
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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