Hydrazine → (2S)-1-((5-ethyl-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-amine

HRID 2369502Notes

Reaction equation

[CH2:1]([CH:3]1[C:12]2=[CH:13][N:14]=[CH:15][CH:16]=[C:11]2[C:10]2[CH:9]=[CH:8][C:7]([O:17][CH2:18][C@@H:19]([N:24]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:6][C:5]=2[O:4]1)[CH3:2].NN>C(O)C.C(Cl)Cl>[CH2:1]([CH:3]1[C:12]2=[CH:13][N:14]=[CH:15][CH:16]=[C:11]2[C:10]2[CH:9]=[CH:8][C:7]([O:17][CH2:18][C@@H:19]([NH2:24])[CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:6][C:5]=2[O:4]1)[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirred solution of 2-((2S)-1-(5-ethyl-5H-chromeno[3,4-c]pyridin-8-yloxy)-4-methylpentan-2-yl)isoindoline-1,3-dione (0.25 g, 0.548 mmol) in ethanol (15 mL) was added hydrazine (0.172 mL, 5.48 mmol) and the reaction mixture was stirred at 40° C. for 6 h. The reaction was cooled to room temperature then diluted with DCM (20 mL) and filtered through a bed of celite. The filtrate was concentrated under reduced pressure and purified by preparative HPLC (0.1% TFA in water and methanol) to yield (2S)-1-((5-ethyl-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-amine (40 mg, 21% yield). The diastereomeric mixture was resolved by SFC (0.5% DEA in methanol).

Workup

temperatureThe reaction was cooled to room temperature
filtrationfiltered through a bed of celite
concentrationThe filtrate was concentrated under reduced pressure
custompurified by preparative HPLC (0.1% TFA in water and methanol)

Sources & evidence

ORD record: ord-2883309596b8446589e13c2278be44e8
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703953B2

Reaction notes

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