Hydrazine → HCID 73214026, compound

HRID 1398391Notes

Reaction equation

[OH:1][C:2]([C:5]1[C:21]([O:22][CH2:23][C@@H:24]([N:29]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:25][CH:26]([CH3:28])[CH3:27])=[CH:20][C:8]2[N:9]([CH3:19])[C:10](=[O:18])[C:11]3[C:16]([C:7]=2[CH:6]=1)=[CH:15][CH:14]=[N:13][C:12]=3[CH3:17])([CH3:4])[CH3:3].NN>C(O)C>[NH2:29][C@@H:24]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:23][O:22][C:21]1[C:5]([C:2]([OH:1])([CH3:3])[CH3:4])=[CH:6][C:7]2[C:16]3[C:11](=[C:12]([CH3:17])[N:13]=[CH:14][CH:15]=3)[C:10](=[O:18])[N:9]([CH3:19])[C:8]=2[CH:20]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (S)-2-(1-((9-(2-hydroxypropan-2-yl)-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)isoindoline-1,3-dione (200 mg, 0.152 mmol) in ethanol (5 mL), was added hydrazine (4.76 μl, 0.152 mmol) at RT then the mixture was heated to 60° C. for 4 h. The reaction mixture was filtered, concentrated and purified by prep. HPLC to afford (S)-8-((2-amino-4-methylpentyl)oxy)-9-(2-hydroxypropan-2-yl)-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one as white solid (9 mg, 0.021 mmol, 14% yield). LC/MS (ESI) m/e 398.0 [(M+H)+, calcd for C23H32N3O3 398.2]; LC/MS retention time (method G): tR=1.99 min. HPLC retention time (method A): tR=8.63 min; HPLC retention time (method B): tR=9.79 min. 1H NMR (400 MHz, METHANOL-d4) ppm 0.94-1.10 (m, 6H), 1.25-1.37 (m, 1H), 1.49-1.78 (m, 7H), 1.82-1.93 (m, 1H), 2.96-3.19 (m, 2H), 3.56-3.65 (m, 1H), 3.80 (s, 3H), 4.16-4.29 (m, 1H), 4.34-4.49 (m, 1H), 7.01-7.15 (m, 1H), 8.10-8.22 (m, 1H), 8.51-8.64 (m, 2H).

Workup

filtrationThe reaction mixture was filtered
concentrationconcentrated
custompurified by prep

Sources & evidence

ORD record: ord-49c0ba2f34d44cb4afc3dcae286564fb
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901305B2

Reaction notes

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