Diisopropylethylamine → HCID 86714759, compound

HRID 1055082Notes

Reaction equation

HRID 1055082 reaction equation
[NH2:1][CH:2]([C:6]([CH3:9])([CH3:8])[CH3:7])[CH2:3][CH2:4][OH:5].[Cl:10][C:11]1[C:16]([C:17]#[N:18])=[CH:15][C:14]([F:19])=[C:13](Cl)[N:12]=1.C(N(CC)C(C)C)(C)C>C(O)C>[Cl:10][C:11]1[C:16]([C:17]#[N:18])=[CH:15][C:14]([F:19])=[C:13]([NH:1][CH:2]([C:6]([CH3:9])([CH3:8])[CH3:7])[CH2:3][CH2:4][OH:5])[N:12]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrileHCID 236606041001428-21-2

Product 1

HCID 86714759HCID 86714759, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 3-amino-4,4-dimethylpentan-1-ol (2.00 g, 8.64 mmol) in ethanol (20 mL) was added racemic 2,6-dichloro-5-fluoro-pyridine-3-carbonitrile (1.65 g, 8.64 mmol) and 5 mL of N,N,-diisopropylethylamine. The solution was stirred at 75° C. for 12 hours and concentrated in vacuo. The residue was purified by silica gel chromatography (methylene chloride), yielding 2.2 g of 2-chloro-5-fluoro-6-(1-hydroxy-4,4-dimethylpentan-3-ylamino)pyridine-3-carbonitrile, 95a: LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, RT=3.02 minutes (M+H) 286.16

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel chromatography (methylene chloride)

Sources & evidence

ORD record
ord-442d0136687e4c52b8971eea95f3a160
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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