3-Amino-4,4,4-trifluorobut-2-enenitrile → rac-4-(6-Fluoro-1H-indazol-5-yl)-2-methyl-6-(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarbonitrile

HRID 1484563Notes

Reaction equation

HRID 1484563 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1/[CH:11]=[C:12](/[C:15](=O)[CH3:16])\[C:13]#[N:14].[NH2:18][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:20][C:21]#[N:22]>>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[CH:11]1[C:20]([C:21]#[N:22])=[C:19]([C:23]([F:26])([F:25])[F:24])[NH:18][C:15]([CH3:16])=[C:12]1[C:13]#[N:14]

Participants

3

Reactant 2

HCID 534010963-Amino-4,4,4-trifluorobut-2-enenitrileHCID 66616240(2E)-2-[(6-fluoro-1H-indazol-5-yl)methylidene]-3-oxobutanenitrile

Product 1

HCID 53232990rac-4-(6-Fluoro-1H-indazol-5-yl)-2-methyl-6-(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarbonitrile

Procedure

Following the procedure described for Example 4, 200 mg (0.87 mmol) (2E)-2-[(6-fluoro-1H-indazol-5-yl)methylidene]-3-oxobutanenitrile (Example 6A) were treated with 3-amino-4,4,4-trifluorobut-2-enenitrile. The crude product was purified by preparative RP-HPLC (acetonitrile/water gradient, final mixture 90:10 v/v) to yield 115 mg (40% of th.) of the racemic title compound.

Workup

  1. customThe crude product was purified by preparative RP-HPLC (acetonitrile/water gradient, final mixture 90:10 v/v)

Sources & evidence

ORD record
ord-6c8b3320076d467ab5be7a511bca52ac
Source dataset
uspto-grants-2016_08
Patent number
US09422263B2

Reaction notes

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