Phenylhydrazine → 4-{(4R)-2,5-Dioxo-7-phenyl-1-[3-(trifluoromethyl)phenyl]-1,2,3,4,5,6,7,8-octahydropyrimido-[4,5-d]pyridazin-4-yl}benzonitrile

HRID 2039697Notes

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][C@H:5]([C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=2)[C:4]=1[C:28](OCC)=[O:29].[C:33]1([NH:39][NH2:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=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:39]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[NH:40][C:28](=[O:29])[C:4]=2[C@@H:5]([C:20]2[CH:21]=[CH:22][C:23]([C:26]#[N:27])=[CH:24][CH:25]=2)[NH:6]1

Participants

Conditions

Temperature: 120 °C

Procedure

80 mg (0.16 mmol) of ethyl (4R)-6-(bromomethyl)-4-(4-cyanophenyl)-2-oxo-1-[3-(tri-fluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate (Example 6A) were dissolved in 2 ml of dioxane, 51 mg (0.47 mmol) of phenylhydrazine were added and the mixture was stirred at 120° C. for 3 hours. The reaction mixture was then concentrated, and the residue that remained was purified by preparative HPLC (Method 10). The product fractions were combined and concentrated, and the solid that remained was dried under reduced pressure (Yield: 24.0 mg, 31% of theory).

Workup

concentrationThe reaction mixture was then concentrated
customthe residue that remained was purified by preparative HPLC (Method 10)
concentrationconcentrated
customthe solid that remained was dried under reduced pressure (Yield: 24.0 mg, 31% of theory)

Sources & evidence

ORD record: ord-495fa6d2a7b147bdb87c233c33cc3afa
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580800B2

Reaction notes

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