Morpholine → HCID 178509518, compound

HRID 1842496Notes

Reaction equation

Cl[C:2]1[C:3]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[NH:18][C:17]4[CH:19]=[CH:20][C:21]([C:23]#[N:24])=[CH:22][C:16]=4[N:15]=3)[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>N1C=CC=CC=1>[N:25]1([C:2]2[C:3]([N:8]3[CH2:9][CH2:10][CH:11]([C:14]4[NH:18][C:17]5[CH:19]=[CH:20][C:21]([C:23]#[N:24])=[CH:22][C:16]=5[N:15]=4)[CH2:12][CH2:13]3)=[N:4][CH:5]=[CH:6][N:7]=2)[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 2-[1-(3-chloro-pyrazin-2-yl)-piperidin-4-yl]-1H-benzoimidazole-5-carbonitrile (150 mg, 0.68 mmol) and morpholine (3 mL) in pyridine was heated at 130° C. under microwave for 45 min. Then it was concentrated to give the crude product which was purified by column chromatography and followed by preparative HPLC to afford pure product 2-[1-(3-morpholin-4-yl-pyrazin-2-yl)-piperidin-4-yl]-1H-benzoimidazole-5-carbonitrile (30 mg, 16%). [M+1] 390. IC50 (uM) 1.996.

Workup

concentrationThen it was concentrated
customto give the crude product which
customwas purified by column chromatography

Sources & evidence

ORD record: ord-df55ebac8f2c4728ab32941c8e4871f0
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946230B2

Reaction notes

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