Diisopropylethylamine → HCID 118162206, compound

HRID 1749421Notes

Reaction equation

HRID 1749421 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:5]=[N+:6]([O-:14])[CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11].CCN(C(C)C)C(C)C.Cl[C:25]1[N:30]=[C:29]([Cl:31])[C:28]([C:32]([F:35])([F:34])[F:33])=[CH:27][N:26]=1>CN(C=O)C.[Cl-].[Na+].O.C(OCC)(=O)C.O>[Cl:31][C:29]1[C:28]([C:32]([F:34])([F:33])[F:35])=[CH:27][N:26]=[C:25]([NH:2][CH2:3][C:4]2[CH:5]=[N+:6]([O-:14])[CH:7]=[CH:8][C:9]=2[C:10]([F:11])([F:12])[F:13])[N:30]=1

Participants

8

Reactant 3

HCID 81531DiisopropylethylamineHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 118162239HCID 118162239, compound

Product 1

HCID 118162206HCID 118162206, compoundYield 47%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-20 °C

Procedure

3-(Aminomethyl)-4-(trifluoromethyl)pyridine 1-oxide hydrochloride (1.0 equiv.) was dissolved in DIEA (2.5 equiv.) and DMF (0.4 M). The homogeneous solution was cooled to −20° C. using an ice and brine bath. To the solution was added 2,4-dichloro-5-(trifluoromethyl)pyrimidine (1.0 equiv.). The solution was stirred for 10 min at −20° C. and then warmed to ambient temperature for 30 min. After 30 min, the solution was diluted with ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate (3×). The organic layers were combined and dried over magnesium sulfate, filtered and the solvent was removed under reduced pressure to afford a white solid. The solid was purified via biotage chromatography (0-60% ethyl acetate in hexanes, then 60% ethyl acetate) to afford the title compound as a white solid (47% yield). MS(ESI) m/z 372.8[M]+.

Workup

  1. temperaturewarmed to ambient temperature for 30 min
  2. waitAfter 30 min
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (3×)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customto afford a white solid
  9. customThe solid was purified via biotage chromatography (0-60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0dc76a661cc54decbd522c068f87811e
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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