Di-tert-butyl azodicarboxylate → 4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-3,5-dimethyl-benzoic acid methyl ester

HRID 417100Notes

Reaction equation

HRID 417100 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.[CH3:35][O:36][C:37](=[O:47])[C:38]1[CH:43]=[C:42]([CH3:44])[C:41]([OH:45])=[C:40]([CH3:46])[CH:39]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>>[CH3:35][O:36][C:37](=[O:47])[C:38]1[CH:43]=[C:42]([CH3:44])[C:41]([O:45][CH2:14][CH:13]([N:12]2[C:11]3[CH:29]=[C:30]([F:34])[C:31]([F:33])=[CH:32][C:10]=3[N:9]=[C:8]2[C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)=[C:40]([CH3:46])[CH:39]=1

Participants

4

Reactant 3

HCID 97268Di-tert-butyl azodicarboxylateHCID 12389264Methyl 4-hydroxy-3,5-dimethylbenzoateHCID 666192022-(4-Chloro-phenyl)-1-(1-cyclohexyl-2-cyclohexylmethoxy-ethyl)-5,6-difluoro-1H-benzoimidazole2×

Product 1

HCID 666196104-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-3,5-dimethyl-benzoic acid methyl ester

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), 4-hydroxy-3,5-dimethyl-benzoic acid methyl ester and replacing di-ethyl azodicarboxylate by di-tert-butyl azodicarboxylate and a reaction time of 18 h. Light yellow solid (12%). MS (Turbo Spray): m/z=553.3 [M+H].

Workup

  1. customa reaction time of 18 h

Sources & evidence

ORD record
ord-50b5e4d72bcb4102af1996756c8ff860
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

Loading…