2-(6-chloropyridin-3-yl)-1H-1,3-benzodiazole → [5-(1H-Benzoimidazol-2-yl)-pyridin-2-yl]-[1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-amine

HRID 913073Notes

Reaction equation

HRID 913073 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[CH2:17]([O:19][C:20]1[CH:21]=[C:22]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:23][N:24]1[CH2:29][CH2:28][CH:27]([NH2:30])[CH2:26][CH2:25]1)[CH3:18]>C(O)CO>[NH:9]1[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=[C:8]1[C:5]1[CH:4]=[CH:3][C:2]([NH:30][CH:27]2[CH2:28][CH2:29][N:24]([CH2:23][C:22]3[CH:31]=[CH:32][C:33]([O:34][CH3:35])=[C:20]([O:19][CH2:17][CH3:18])[CH:21]=3)[CH2:25][CH2:26]2)=[N:7][CH:6]=1

Participants

4

Reactant 2

HCID 14883902-(6-chloropyridin-3-yl)-1H-1,3-benzodiazoleHCID 392574451-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine2×

Product 1

HCID 24855022[5-(1H-Benzoimidazol-2-yl)-pyridin-2-yl]-[1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-amineYield 9%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A solution of 2-(6-chloro-pyridin-3-yl)-1H-benzoimidazole (23.0 mg, 0.10 mmol, 1.0 equiv; commercially available) and 1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine (39.7 mg, 0.15 mmol, 1.5 equiv; intermediate A1) in ethylene glycol (2 mL) was heated by microwave irradiation to 220° C. for 20 min. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 4.0 mg (9%) of the title compound. MS (ISP): 456.6 [M−H]−.

Workup

  1. customRemoval of the solvent
  2. customunder reduced pressure and purification by preparative HPLC on reversed phase
  3. washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-4acfdb6e85304c2e83e4e66dd9eba7ff
Source dataset
uspto-grants-2011_09
Patent number
US08026255B2

Reaction notes

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