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

HRID 410216Notes

Reaction equation

HRID 410216 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

5

Reactant 2

HCID 593271274-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)anilineHCID 1784889662-chloro-4-methoxy-1H-Benzimidazole

Product 1

HCID 178488987HCID 178488987, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

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

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

Sources & evidence

ORD record
ord-8942d9e675d24fbca13a12318c444dd1
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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