Di-tert-butyl azodicarboxylate → HCID 66619228, compound

HRID 417109Notes

Reaction equation

[CH:1]1([CH:7]([N:10]2[C:14]3[CH:15]=[C:16]([F:20])[C:17]([F:19])=[CH:18][C:13]=3[N:12]=[C:11]2[C:21]2[C:22]([O:29][CH3:30])=[N:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[CH2:8][OH:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O[C:32]1[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][N:33]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>>[CH3:39][O:38][C:36](=[O:37])[C:35]1[CH:40]=[CH:41][C:32]([O:9][CH2:8][CH:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:10]2[C:14]3[CH:15]=[C:16]([F:20])[C:17]([F:19])=[CH:18][C:13]=3[N:12]=[C:11]2[C:21]2[C:22]([O:29][CH3:30])=[N:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)=[N:33][CH:34]=1

Participants

Reactant 3

HCID 97268Di-tert-butyl azodicarboxylate

HCID 66619606HCID 66619606, compound

HCID 178498304HCID 178498304, compound

Product 1

HCID 66619228HCID 66619228, compoundYield 4%

Procedure

The title compound was prepared in analogy to Example 4, intermediate from 2-cyclohexyl-2-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-ethanol and methyl 6-hydroxynicotinate (commercially available) and replacing di-ethyl azodicarboxylate by di-tert-butyl azodicarboxylate. The crude product 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 60:40) to give the desired compound as a white solid (4%). MS (Turbo Spray) m/z=553.4 [M+H].

Workup

customThe crude product was purified by silica gel chromatography
washeluting with a gradient of n-heptane:ethyl acetate (100:0 to 60:40)

Sources & evidence

ORD record: ord-902586d27f364aa4ab35db5114ae752d
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088930B2

Reaction notes

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