tert-Butyl carbazate → 2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl)-4-fluoro-benzoic Acid, 2-(1,1-dimethylethyloxy)carbonyl Hydrazide

HRID 1835052Notes

Reaction equation

HRID 1835052 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]2=[O:24])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[C:25]([O:29][C:30](=[O:33])[NH:31][NH2:32])([CH3:28])([CH3:27])[CH3:26]>O1CCCC1>[CH3:26][C:25]([CH3:28])([O:29][C:30]([NH:31][NH:32][C:4](=[O:5])[C:3]1[CH:7]=[C:8]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:20])([F:22])[F:21])[N:14]([CH3:23])[C:13]2=[O:24])[C:9]([F:11])=[CH:10][C:2]=1[Cl:1])=[O:33])[CH3:27]

Participants

4

Reactant 2

HCID 70091tert-Butyl carbazateHCID 116324172-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl)-4-fluoro-benzoyl Chloride

Product 1

HCID 116199632-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl)-4-fluoro-benzoic Acid, 2-(1,1-dimethylethyloxy)carbonyl HydrazideYield 76.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl)-4-fluoro-benzoyl chloride (0.5 g) in tetrahydrofuran (20 ml) was added t-butylcarbazate (0.18 g) at ambient temperature. After 1 hour, the resulting mixture was concentrated under reduced pressure and the residue was subjected to column chromatography on silica gel eluted with a mixed solvent of ethyl acetate and hexane (2:3) to give the titled compound (0.48 g).

Workup

  1. concentrationthe resulting mixture was concentrated under reduced pressure
  2. washeluted with a mixed solvent of ethyl acetate and hexane (2:3)

Sources & evidence

ORD record
ord-b220d17697dc421d87294c6f61834638
Source dataset
uspto-grants-2004_08
Patent number
US06770597B2

Reaction notes

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