Triethylamine → Tert-butyl 4-(4-(1-(pyridazin-3-yl)azetidine-3-carboxamido)phenyl)piperidine-1-carboxylate

HRID 873567Notes

Reaction equation

Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:11][CH:10]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH:21]4[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)=[O:13])[CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.C1CC=CCC=1>[Pd]>[N:7]1[CH:2]=[CH:3][CH:4]=[C:5]([N:8]2[CH2:11][CH:10]([C:12]([NH:14][C:15]3[CH:16]=[CH:17][C:18]([CH:21]4[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:25][CH2:26]4)=[CH:19][CH:20]=3)=[O:13])[CH2:9]2)[N:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a 50 mL round-bottomed flask was added tert-butyl 4-(4-(1-(6-chloropyridazin-3-yl)azetidine-3-carboxamido)phenyl)piperidine-1-carboxylate (550 mg, 1.165 mmol) and Pd/C (93 mg, 0.087 mmol). The flask was flushed with nitrogen for 10 minutes and ethanol (11.7 ml) was added. Triethylamine (0.162 ml, 1.165 mmol) and cyclohexa-1,4-diene (654 mg, 8.16 mmol) were added and the reaction was stirred at 80° C. for 1 hour, cooled and filtered through diatomaceous earth. The filtrate was concentrated in vacuo and the residue was purified by regular phase flash column chromatography to give the title compound.

Workup

customThe flask was flushed with nitrogen for 10 minutes
additionethanol (11.7 ml) was added
temperaturecooled
filtrationfiltered through diatomaceous earth
concentrationThe filtrate was concentrated in vacuo
customthe residue was purified by regular phase flash column chromatography

Sources & evidence

ORD record: ord-a82ea6b1561f4fc09794abf23a3a08cc
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975398B2

Reaction notes

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