tert-Butyl carbazate → HCID 67067180, compound

HRID 599558Notes

Reaction equation

HRID 599558 reaction equation
C1C=CC2N(O)N=NC=2C=1.FC(F)(F)C(O)=O.[Cl:18][CH2:19][CH2:20][CH2:21]/[C:22](=[CH:26]\[C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34]2)=[C:29]([O:39][CH3:40])[CH:28]=1)/[C:23]([OH:25])=O.[C:41]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])(=[O:44])[NH:42][NH2:43].C(N(C(C)C)CC)(C)C.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[Cl:18][CH2:19][CH2:20][CH2:21]/[C:22](=[CH:26]\[C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34]2)=[C:29]([O:39][CH3:40])[CH:28]=1)/[C:23]([NH:43][NH:42][C:41]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])=[O:25]

Participants

9

Reactant 5

HCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66960186(E)-5-chloro-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)valeric acid trifluoroacetateHCID 86585896Sodium bicarbonate water

Product 1

HCID 67067180HCID 67067180, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

HOBT (108 mg) and EDC (153 mg) were sequentially added to a solution of 5-chloro-2-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}valeric acid trifluoroacetic acid salt (300 mg), tert-butyl carbazate (71 mg) and IPEA (0.38 mL) in DMF (5 mL), and the reaction solution was stirred at room temperature for three hours. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: heptane:ethyl acetate=1:1→ethyl acetate) to obtain 222 mg of the title compound. The property value of the compound is as follows.

Workup

  1. customthe organic layer was separated
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: heptane:ethyl acetate=1:1→ethyl acetate)

Sources & evidence

ORD record
ord-6b62e2ffcd754f49aa716544549b0e6a
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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