(S)-3-Amino-1-benzylpiperidine → (S)-6-(1-benzylpiperidin-3-ylamino)-8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazine-3-carbonitrile

HRID 2239889Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([N:13]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]2[N:6]([C:8]([C:11]#[N:12])=[CH:9][N:10]=2)[N:7]=1.[NH2:29][C@H:30]1[CH2:35][CH2:34][CH2:33][N:32]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:31]1>C(Cl)Cl>[CH2:36]([N:32]1[CH2:33][CH2:34][CH2:35][C@H:30]([NH:29][C:2]2[CH:3]=[C:4]([N:13]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:5]3[N:6]([C:8]([C:11]#[N:12])=[CH:9][N:10]=3)[N:7]=2)[CH2:31]1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

Conditions

Temperature: 160 °C

Procedure

6-Chloro-8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazine-3-carbonitrile (100 mg, 0.257 mmol) from example XXXI, step (1b) and (S)-3-amino-1-benzylpiperidine (195 mg, 1.026 mmol) were combined in a 1-dram vial and heated at 160° C. for 6 h. The reaction was cooled to room temperature, dissolved in DCM (2 mL) and loaded onto to a 12 g silica gel column and eluted with 5%-100% EtOAc/heptane to give (S)-6-(1-benzylpiperidin-3-ylamino)-8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazine-3-carbonitrile (55 mg, 40%). LCMS m/z (544, M+1).

Workup

temperatureThe reaction was cooled to room temperature
washeluted with 5%-100% EtOAc/heptane

Sources & evidence

ORD record: ord-3a9e3131a6764076b7039921f4ec0983
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723336B2

Reaction notes

Loading…