Water → 2-(6-Chloro-5-cyano-3-fluoropyridin-2-ylamino)-4,4,4-trifluorobutanamide

HRID 2201157

Reaction equation

HRID 2201157 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([F:10])=[C:4](Cl)[N:3]=1.Cl.[NH2:13][CH:14]([CH2:18][C:19]([F:22])([F:21])[F:20])[C:15]([NH2:17])=[O:16].CCN(C(C)C)C(C)C.O>CS(C)=O.CCOC(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:13][CH:14]([CH2:18][C:19]([F:22])([F:21])[F:20])[C:15]([NH2:17])=[O:16])[C:5]([F:10])=[CH:6][C:7]=1[C:8]#[N:9]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrileHCID 866661692-Amino-4,4,4-trifluorobutanamide hydrochloride

Product 1

HCID 866661702-(6-Chloro-5-cyano-3-fluoropyridin-2-ylamino)-4,4,4-trifluorobutanamideYield 100.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,6-dichloro-3-cyano-5-fluoropyridine (134 mg, 0.701 mmol), 2-amino-4,4,4-trifluorobutanamide hydrochloride (135 mg, 0.701 mmol) and DIEA (0.365 mL, 2.10 mmol) in DMSO (3 mL) was stirred at 95 C for 3 h. Water and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo to give crude 2-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)-4,4,4-trifluorobutanamide (218 mg).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bda6df5e46194038996ce7ea5e9c5af5
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Linked notes

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