Triethylamine → 2-(3-(3-(3-(Pyridin-3-yl)pyrrolidin-1-yl)pyrazin-2-yl)azetidin-1-yl)quinoline

HRID 1850321Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

To a 3 mL vial was added 2-(3-(3-chloropyrazin-2-yl)azetidin-1-yl)quinoline (0.04000 g, 0.135 mmol), 3-(pyrrolidin-3-yl)pyridine (commerically available at Array Biopharma, 0.040 g, 0.270 mmol), and triethylamine (commerically available at Sigma Aldrich, 0.038 ml, 0.270 mmol) in DMSO (Solvent Volume: 0.449 ml) and the reaction was stirred at 110° C. overnight. Upon completion, the reaction was filtered into a 24 well plate and purified by reverse phase purification using the following conditions: (Instrumentation: MS—Waters SQ; UV—Waters 2487 or Waters PD; Solvents: A: Water w/0.1% NH4OH B: Acetonitrile w/0.1% NH4OH; Column: Phenomenex Gemini-NX C18 110A 5 um 21×100; Flow Rate: 44 mL/min. 10 min Method, variable gradient over 8 mins.)

Workup

filtrationUpon completion, the reaction was filtered into a 24 well plate
custompurified by reverse phase purification
wait10 min Method, variable gradient over 8 mins

Sources & evidence

ORD record: ord-db376689e1894799817c6a12ff5a91b0
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957073B2

Reaction notes

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