Hydrazine hydrate (1:1) → HCID 16222361, compound

HRID 1435972Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:21]([N:25]2C(=O)C4C(=CC=CC=4)C2=O)=[N:20][CH:19]=[CH:18]3)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>C(O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:21]([NH2:25])=[N:20][CH:19]=[CH:18]3)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the above (S)-2-[6-(1-benzylpiperidin-3-yloxy)isoquinolin-1-yl]-isoindole-1,3-dione (20 mg, 43 μmol) in ethanol (2 ml) was added hydrazine monohydrate (−3 μL, 65 μmol). The mixture was heated at 50° C. for 2 h then concentrated in vacuo to give a residue. The residue was purified by prep-HPLC to give (S)-6-(1-benzylpiperidine-3-yloxy)isoquinolin-1-yl amine El-MS: m/z=334.3 [M+H]+.

Workup

concentrationthen concentrated in vacuo
customto give a residue
customThe residue was purified by prep-HPLC

Sources & evidence

ORD record: ord-923fdd40e7f44e10ab95054374512752
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618985B2

Reaction notes

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