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

HRID 528513Notes

Reaction equation

HRID 528513 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][N:10]2[C:18]3([CH2:20][CH2:19]3)[C:17]3[CH:16]=[C:15]4[O:21][CH2:22][O:23][C:14]4=[CH:13][C:12]=3[C:11]2=[O:24])[CH2:4][CH2:3]1.Br.Br[CH2:27][C:28]1[N:29]=[N:30][CH:31]=[CH:32][CH:33]=1>>[N:30]1[CH:31]=[CH:32][CH:33]=[C:28]([CH2:27][N:2]2[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][N:10]3[C:18]4([CH2:20][CH2:19]4)[C:17]4[CH:16]=[C:15]5[O:21][CH2:22][O:23][C:14]5=[CH:13][C:12]=4[C:11]3=[O:24])[CH2:4][CH2:3]2)[N:29]=1

Participants

3

Reactant 2

HCID 714640243-(Bromomethyl)pyridazine hydrobromideHCID 1180573846-[2-(4-Piperidyl)ethyl]spiro[[1,3]dioxolo[4,5-f]isoindole-7,1'-cyclopropane]-5-one hydrochloride

Product 1

HCID 729443206-[2-[1-(Pyridazin-3-ylmethyl)-4-piperidyl]ethyl]spiro[[1,3]dioxolo[4,5-f]isoindole-7,1'-cyclopropane]-5-one

Procedure

Compound I-38 was prepared according to the method in example 42, using 6-[2-(4-piperidyl)ethyl]spiro[[1,3]dioxolo[4,5-f]isoindole-7,1′-cyclopropane]-5-one hydrochloride (compound II-5) and 3-bromomethylpyridazine hydrobromide as the raw materials: 1H NMR(CDCl3): δ 1.25-1.37 (m, 5H), 1.49-1.58 (m, 4H), 1.73 (d, 2H, J=11.2 Hz), 2.14 (t, 2H, J=10.7 Hz), 2.82 (d, 2H, J=11.6 Hz), 3.19 (t, 2H, J=7.8 Hz), 3.85 (s, 2H), 6.03 (s, 2H), 6.43 (s, 1H), 7.23 (s, 1H), 7.46 (dd, 1H, J=8.4, 4.9 Hz), 7.67 (d, 1H, J=8.0 Hz), 9.08 (dd, 1H, J=4.8, 1.4 Hz): m/z 407 [M+H]+.

Workup

  1. customCompound I-38 was prepared

Sources & evidence

ORD record
ord-499dddcaab76475d809e1f9ff584159e
Source dataset
uspto-grants-2016_05
Patent number
US09346818B2

Reaction notes

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