Acrylonitrile → HCID 67374206, compound

HRID 2168632Notes

Reaction equation

HRID 2168632 reaction equation
Cl.Cl.[CH2:3]([C:7]1[N:8]=[N:9][C:10]([O:26][CH:27]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:15][CH:14]=1)[CH2:4][CH2:5][CH3:6].[C:34](#[N:37])[CH:35]=C>>[CH2:3]([C:7]1[N:8]=[N:9][C:10]([O:26][CH:27]2[CH2:32][CH2:31][N:30]([CH2:33][CH2:35][C:34]#[N:37])[CH2:29][CH2:28]2)=[CH:11][C:12]=1[C:13]1[CH:14]=[CH:15][C:16]([O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:17][CH:18]=1)[CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 2

HCID 7855AcrylonitrileHCID 53373967HCID 53373967, compound

Product 1

HCID 67374206HCID 67374206, compound

Procedure

A mixture of 3-butyl-4-(4-cyclohexyloxy-phenyl)-6-(piperidin-4-yloxy)-pyridazine (Example 14, 0.244 mmol, 100 mg) and acrylonitrile (1 mL) may be stirred at room temperature for 20 h. The organic solvent may be removed in vacuo, and the residue may be purified by column chromatography on silica gel using 1-2% of MeOH in DCM to provide 3-{4-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-piperidin-1-yl}-propionitrile.

Workup

  1. customThe organic solvent may be removed in vacuo
  2. customthe residue may be purified by column chromatography on silica gel using 1-2% of MeOH in DCM

Sources & evidence

ORD record
ord-b73889c3e2e14f67bce85eace998d908
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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