Triethylamine → Ethyl 3-[(6-chloro-5-cyano-3-fluoro-2-pyridyl)amino]-4,4-dimethyl-hexanoate

HRID 1055123Notes

Reaction equation

HRID 1055123 reaction equation
[NH2:1][CH:2]([C:9]([CH3:13])([CH3:12])[CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:14][C:15]1[C:20]([C:21]#[N:22])=[CH:19][C:18]([F:23])=[C:17](Cl)[N:16]=1.CCN(CC)CC>C(#N)C>[Cl:14][C:15]1[N:16]=[C:17]([NH:1][CH:2]([C:9]([CH3:12])([CH3:13])[CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:18]([F:23])=[CH:19][C:20]=1[C:21]#[N:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrileHCID 86714737HCID 86714737, compound2×

Product 1

HCID 86714774Ethyl 3-[(6-chloro-5-cyano-3-fluoro-2-pyridyl)amino]-4,4-dimethyl-hexanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl 3-amino-4,4-dimethyl-hexanoate, 27a, (0.24 g, 1.28 mmol), 2,6-dichloro-5-fluoro-pyridine-3-carbonitrile (0.29 g, 1.53 mmol) and Et3N (0.43 mL, 3.07 mmol) in acetonitrile (4.8 mL) was stirred at 70° C. overnight. The reaction mixture was concentrated in vacuo and purified by silica gel chromatography (10-40% EtOAc/Hexanes gradient) to provide 205 mg of ethyl 3-[(6-chloro-5-cyano-3-fluoro-2-pyridyl)amino]-4,4-dimethyl-hexanoate; LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, Retention Time=3.75 minutes (M+H) 342.04.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by silica gel chromatography (10-40% EtOAc/Hexanes gradient)

Sources & evidence

ORD record
ord-85a9f3c75ad54b9c8a027ad7d34ddf48
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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