N,N,N',N'-Tetramethylazodicarboxamide → HCID 66619249, compound

HRID 417131Notes

Reaction equation

HRID 417131 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.[OH:35][C:36]1[CH:48]=[CH:47][C:39]([O:40][C:41]2([C:44]([OH:46])=[O:45])[CH2:43][CH2:42]2)=[CH:38][CH:37]=1.[CH3:49]N(C)C(N=NC(N(C)C)=O)=O>>[CH3:49][O:45][C:44]([C:41]1([O:40][C:39]2[CH:38]=[CH:37][C:36]([O:35][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:48][CH:47]=2)[CH2:43][CH2:42]1)=[O:46]

Participants

4

Reactant 3

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 666192022-(4-Chloro-phenyl)-1-(1-cyclohexyl-2-cyclohexylmethoxy-ethyl)-5,6-difluoro-1H-benzoimidazole2×HCID 66619486HCID 66619486, compound

Product 1

HCID 66619249HCID 66619249, compound

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)-cyclopropanecarboxylic acid (CAS RN: 857903-44-7) 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 (31%). MS (Turbo Spray): m/z=581.2 [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-8a395f9b2e73471e85fe8e9297dae44a
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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