4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)aniline → HCID 178488987, compound

HRID 1880083Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:8]([O:13][C:14]3[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=3)=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.Cl[C:22]1[NH:26][C:25]2[C:27]([O:31][CH3:32])=[CH:28][CH:29]=[CH:30][C:24]=2[N:23]=1>CC(O)C.O>[CH3:32][O:31][C:27]1[C:25]2[NH:26][C:22]([NH:18][C:17]3[CH:16]=[CH:15][C:14]([O:13][C:8]4[C:7]([CH:4]5[CH2:3][CH2:2][O:1][CH2:6][CH2:5]5)=[CH:12][CH:11]=[CH:10][N:9]=4)=[CH:20][CH:19]=3)=[N:23][C:24]=2[CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A glass microwave reaction vessel was charged with 4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)aniline (0.1130 g, 0.418 mmol) and 2-chloro-7-methoxy-1H-benzo[d]imidazole (0.092 g, 0.502 mmol) in IPA. The reaction mixture was stirred and heated in a Biotage Initiator microwave reactor at 170° C. for 30 min. The reaction mixture was diluted with water and extracted with DCM. The organic extract was washed with water, brine, dried with magnesium sulfate, filtered, and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage pre-packed silica gel column (40S), eluting with a gradient of 1% to 5% MeOH in DCM, to provide 7-methoxy-N-(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine. MS (ESI, pos. ion) m/z: 417.0 (M+1). IC50 (uM) +++++.

Workup

customA glass microwave reaction vessel
extractionextracted with DCM
extractionThe organic extract
washwas washed with water, brine
dry with materialdried with magnesium sulfate
filtrationfiltered
concentrationconcentrated
customchromatographed through a Biotage pre-packed silica gel column (40S)
washeluting with a gradient of 1% to 5% MeOH in DCM

Sources & evidence

ORD record: ord-cc0c4a175a1e4751b0d3a33fe1c81921
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318718B2

Reaction notes

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