3-(Bromomethyl)pyridazine hydrobromide → 6-[2-[1-(Pyridazin-3-ylmethyl)-4-piperidyl]ethyl]-[1,3]dioxolo[4,5-f]isoindole-5,7-dione

HRID 528512Notes

Reaction equation

HRID 528512 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][N:10]2[C:18](=[O:19])[C:17]3[CH:16]=[C:15]4[O:20][CH2:21][O:22][C:14]4=[CH:13][C:12]=3[C:11]2=[O:23])[CH2:4][CH2:3]1.Br.Br[CH2:26][C:27]1[N:28]=[N:29][CH:30]=[CH:31][CH:32]=1>>[N:29]1[CH:30]=[CH:31][CH:32]=[C:27]([CH2:26][N:2]2[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][N:10]3[C:18](=[O:19])[C:17]4[CH:16]=[C:15]5[O:20][CH2:21][O:22][C:14]5=[CH:13][C:12]=4[C:11]3=[O:23])[CH2:4][CH2:3]2)[N:28]=1

Participants

3

Reactant 2

HCID 714640243-(Bromomethyl)pyridazine hydrobromideHCID 1180573866-[2-(4-Piperidyl)ethyl]-[1,3]dioxolo[4,5-f]isoindole-5,7-dione hydrochloride

Product 1

HCID 729443196-[2-[1-(Pyridazin-3-ylmethyl)-4-piperidyl]ethyl]-[1,3]dioxolo[4,5-f]isoindole-5,7-dione

Procedure

Compound I-37 was prepared according to the method in example 3, using 6-[2-(4-piperidyl)ethyl]-[1,3]dioxolo[4,5-f]isoindole-5,7-dione hydrochloride (compound II-1) and 3-bromomethylpyridazine hydrobromide as the raw materials: 1H NMR (CDCl3): δ 1.26-1.32 (m, 3H), 1.58 (q, 2H, J=5.0 Hz), 1.75 (d, 2H, J=8.9 Hz), 2.12 (t, 2H, J=10.6 Hz), 2.81 (d, 2H, J=11.1 Hz), 3.65 (t, 2H, J=7.2 Hz), 3.84 (s, 2H), 6.15 (s, 2H), 7.19 (s, 2H), 7.45 (dd, 1H, J=8.4, 4.9 Hz), 7.66 (dd, 1H, J=8.4, 1.2 Hz), 9.07 (dd, 1H, J=4.8, 1.6 Hz): m/z 395 [M+H]+.

Workup

  1. customCompound I-37 was prepared

Sources & evidence

ORD record
ord-a41d392b022b4b8f950d7cdfc716a392
Source dataset
uspto-grants-2016_05
Patent number
US09346818B2

Reaction notes

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