Phenylhydrazine → HCID 44480787, compound

HRID 2039698Notes

Reaction equation

HRID 2039698 reaction equation
Br[CH2:2][C:3]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:7](=[O:19])[NH:6][CH:5]([C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][C:21]=2[S:28]([CH3:31])(=[O:30])=[O:29])[C:4]=1[C:32](OCC)=[O:33].[C:37]1([NH:43][NH2:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O1CCOCC1>[O:19]=[C:7]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[CH:10]=2)[C:3]2[CH2:2][N:43]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[NH:44][C:32](=[O:33])[C:4]=2[CH:5]([C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][C:21]=2[S:28]([CH3:31])(=[O:29])=[O:30])[NH:6]1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 58133724HCID 58133724, compound

Product 1

HCID 44480787HCID 44480787, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 6-(bromomethyl)-4-[4-cyano-2-(methylsulphonyl)phenyl]-2-oxo-1-[3-(trifluoromethyl)-phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate (150 mg, 0.256 mmol; Example 19A) was initially charged in dioxane (3.5 ml). Phenylhydrazine (83.0 mg, 0.767 mmol) was added dropwise to the reaction mixture, and the mixture was then stirred at boiling point for 3 h. The reaction mixture was then separated directly by preparative HPLC (Method 12). This gave 9 mg (6% of theory) of the target compound.

Workup

  1. customfor 3 h
  2. customThe reaction mixture was then separated directly by preparative HPLC (Method 12)

Sources & evidence

ORD record
ord-1a3d2c296ad04a8986a28ecaf9fb914a
Source dataset
uspto-grants-2013_11
Patent number
US08580800B2

Reaction notes

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