N,N,N',N'-Tetramethylazodicarboxamide → HCID 66619245, compound

HRID 417123Notes

Reaction equation

HRID 417123 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:14][OH:15])[C:11]3[CH:22]=[C:23]([F:27])[C:24]([F:26])=[CH:25][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.O[C:29]1[CH:39]=[CH:38][C:32]([O:33][CH2:34][C:35]([OH:37])=[O:36])=[C:31]([CH3:40])[CH:30]=1.[CH2:41](P(CCCC)CCCC)[CH2:42]CC.CN(C)C(N=NC(N(C)C)=O)=O>>[CH2:41]([O:37][C:35](=[O:36])[CH2:34][O:33][C:32]1[CH:38]=[CH:39][C:29]([O:15][CH2:14][CH:13]([N:12]2[C:11]3[CH:22]=[C:23]([F:27])[C:24]([F:26])=[CH:25][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:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)=[CH:30][C:31]=1[CH3:40])[CH3:42]

Participants

5

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 21908068(4-Hydroxy-2-methylphenoxy)acetic acidHCID 666193102-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanol

Product 1

HCID 66619245HCID 66619245, compoundYield 16%

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 (Ex. 1, int. c), (4-hydroxy-2-methyl-phenoxy)-acetic acid (CAS RN 317319-10-1), tri-n-butylphosphin and N,N,N′,N′-tetramethylazodicarboxamide. The residue 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) to give the title compound as a light yellow foam (16%). MS (Turbo Spray): m/z=583.3 [M+H].

Workup

  1. customThe residue 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-ab07d48170b74142b55713725a8047a2
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

Loading…