N,N,N',N'-Tetramethylazodicarboxamide → 1-(4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-phenoxy)-cyclobutanecarboxylic acid ethyl ester

HRID 417130Notes

Reaction equation

HRID 417130 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][O:15]CC3CCCCC3)[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.[CH2:35]([O:37][C:38]([C:40]1([O:44][C:45]2[CH:50]=[CH:49][C:48](O)=[CH:47][CH:46]=2)[CH2:43][CH2:42][CH2:41]1)=[O:39])[CH3:36].C(P(CCCC)CCCC)CCC.CN(C)C(N=NC(N(C)C)=O)=O>>[CH2:35]([O:37][C:38]([C:40]1([O:44][C:45]2[CH:50]=[CH:49][C:48]([O:15][CH2:14][CH:13]([N:12]3[C:11]4[CH:29]=[C:30]([F:34])[C:31]([F:33])=[CH:32][C:10]=4[N:9]=[C:8]3[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:47][CH:46]=2)[CH2:43][CH2:42][CH2:41]1)=[O:39])[CH3:36]

Participants

5

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 59723885Ethyl 1-(4-hydroxyphenoxy)-1-cyclobutanecarboxylateHCID 666192022-(4-Chloro-phenyl)-1-(1-cyclohexyl-2-cyclohexylmethoxy-ethyl)-5,6-difluoro-1H-benzoimidazole2×

Product 1

HCID 666194041-(4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-phenoxy)-cyclobutanecarboxylic acid ethyl 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), 1-(4-hydroxy-phenoxy)-cyclobutanecarboxylic acid ethyl ester (CAS RN: 879094-83-4), tri-n-butylphosphin and N,N,N′,N′-tetramethylazodicarboxamide. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 70:30). Light yellow foam (45%). MS (Turbo Spray): m/z=609.3 [M+H].

Workup

  1. customThe compound was purified by silica gel chromatography
  2. washeluting with a gradient of n-heptane:ethyl acetate (100:0 to 70:30)

Sources & evidence

ORD record
ord-60f2548602444f0c9569461269301303
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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