Diisopropylethylamine → HCID 86663355, compound

HRID 2178294Notes

Reaction equation

HRID 2178294 reaction equation
[CH3:1][CH:2]([CH3:10])[CH:3]([C@H:5]1[CH2:9][CH2:8][NH:7][CH2:6]1)[NH2:4].[Cl:11][C:12]1[C:17]([C:18]#[N:19])=[CH:16][C:15]([F:20])=[C:14](Cl)[N:13]=1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.CCOC(C)=O.O.C([O-])(O)=O.[Na+]>[NH2:4][C@H:3]([C@@H:5]1[CH2:9][CH2:8][N:7]([C:14]2[C:15]([F:20])=[CH:16][C:17]([C:18]#[N:19])=[C:12]([Cl:11])[N:13]=2)[CH2:6]1)[CH:2]([CH3:10])[CH3:1]

Participants

8

Reactant 3

HCID 81531DiisopropylethylamineHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrileHCID 66796681HCID 66796681, compound

Product 1

HCID 86663355HCID 86663355, compoundYield 86.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-methyl-1-[(3S)-pyrrolidin-3-yl]propan-1-amine (310 mg, 1.98 mmol), 2,6-dichloro-5-fluoro-pyridine-3-carbonitrile (378.7 mg, 1.98 mmol) and DIPEA (512.6 mg, 690.8 μL, 3.97 mmol) in NMP (3 mL) was heated at 130° C. for 20 minutes under microwave conditions. After this time, the reaction mixture was allowed to cool to ambient temperature and diluted with EtOAc, water and saturated aqueous NaHCO3. The organic layer was separated and washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude mixture was purified by column chromatography (ISCO Companion™, 40 g column, eluting with MeOH/DCM) to give the sub title compound as an oil (506.3 mg, 86% Yield).

Workup

  1. temperatureto cool to ambient temperature
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude mixture was purified by column chromatography (ISCO Companion™, 40 g column, eluting with MeOH/DCM)

Sources & evidence

ORD record
ord-a301786b574c4974bf860dfe71262b07
Source dataset
uspto-grants-2015_06
Patent number
US09067932B2

Reaction notes

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