Di-tert-butyl azodicarboxylate → 6-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-nicotinonitrile

HRID 417101Notes

Reaction equation

HRID 417101 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:14]OCC3CCCCC3)[C:11]3[CH:29]=[C:30]([F:34])[C:31]([F:33])=[CH:32][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[C:35]([C:37]1[CH:38]=[N:39][C:40]([OH:43])=[CH:41][CH:42]=1)#[N:36].N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)[CH2:14][O:43][C:40]3[CH:41]=[CH:42][C:37]([C:35]#[N:36])=[CH:38][N:39]=3)[C:11]3[CH:29]=[C:30]([F:34])[C:31]([F:33])=[CH:32][C:10]=3[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 97268Di-tert-butyl azodicarboxylateHCID 70621976-HydroxynicotinonitrileHCID 666192022-(4-Chloro-phenyl)-1-(1-cyclohexyl-2-cyclohexylmethoxy-ethyl)-5,6-difluoro-1H-benzoimidazole2×

Product 1

HCID 666192476-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-nicotinonitrile

Procedure

The title compound was prepared in analogy to Example 4, intermediate, from 2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanol (Example 1, intermediate c), 3-cyano-6-hydroxy-pyridine and replacing di-ethyl azodicarboxylate by di-tert-butyl azodicarboxylate and a reaction time of 18 h. Light yellow solid (41%). MS (Turbo Spray): m/z=493.2 [M+H].

Workup

  1. customa reaction time of 18 h

Sources & evidence

ORD record
ord-e0784486142743838ad193d295c0cb96
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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