Water → HCID 69481020, compound

HRID 2364366Notes

Reaction equation

O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][CH2:14][N:15]1[C:24]2[C:19](=[N:20][CH:21]=[C:22]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH:23]=2)[C:18]([OH:33])=[C:17]([C:34]([NH:36][CH2:37][CH2:38][O:39][CH2:40][CH3:41])=[O:35])[C:16]1=[O:42].NN.O>C(O)C>[NH2:3][CH2:12][CH2:13][CH2:14][N:15]1[C:24]2[C:19](=[N:20][CH:21]=[C:22]([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)[CH:23]=2)[C:18]([OH:33])=[C:17]([C:34]([NH:36][CH2:37][CH2:38][O:39][CH2:40][CH3:41])=[O:35])[C:16]1=[O:42]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (261 mg, 0.46 mmol) and anhydrous hydrazine (286 μL, 9.1 mmol) in ethanol (20 mL) was heated at 50° C. for 5 hours. Water (40 mL) was added and the resulting slurry was cooled to 0-5° C. and collected by filtration to provide the product as a white solid: 1H NMR (CDCl3) δ 10.52 (1H, b), 8.44 (1H, s), 7.93 (1H, s), 7.33-7.39 (2H, m), 7.09-7.16 (2H, m), 4.22 (2H, t, J=7 Hz), 4.13 (2H, s), 3.42-3.50 (6H, m), 2.61 (2H, t, J=7 Hz), 1.65-1.73 (2H, m), 1.11 (3H, t, J=7 Hz); ES+ MS: 443 (M+H+).

Workup

temperaturethe resulting slurry was cooled to 0-5° C.
filtrationcollected by filtration

Sources & evidence

ORD record: ord-4dbb97daa4b5433082c6c25b9599aa8a
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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