2,4-Dichloro-1,3,5-triazine → 1-(4-Chloro-[1,3,5]triazin-2-yl)-7-trifluoromethyl-1,2,3,4-tetrahydro-quinoline

HRID 1815899Notes

Reaction equation

[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][NH:10]2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[Cl:24][C:25]1[N:30]=[C:29](Cl)[N:28]=[CH:27][N:26]=1>CN(C=O)C>[Cl:24][C:25]1[N:30]=[CH:29][N:28]=[C:27]([N:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:12]=3)[CH2:7][CH2:8][CH2:9]2)[N:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

7-(Trifluoromethyl)-1,2,3,4-tetrahydroquinoline (440 mg, 2.2 mmol) was dissolved in DMF (10 mL) under N2 at room temperature. DIEA (284 mg, 2.2 mmol) was added, and the reaction solution was cooled to 0° C. 2,4-Dichloro-1,3,5-triazine was added, and reaction was stirred with gradual warming to RT. The reaction was quenched after 3 h with water, which caused a fine precipitate to form, which is not filterable. This mixture was extracted 3 times with EtOAc. The EtOAc extracts were then washed brine, combined, dried over Na2SO4, filtered, concentrated, and dried under high vacuum giving 1-(4-chloro-[1,3,5]triazin-2-yl)-7-trifluoromethyl-1,2,3,4-tetrahydro-quinoline (800 mg (>100%)) of a yellow oil that was used without further purification.

Workup

customreaction
temperaturewith gradual warming to RT
customThe reaction was quenched after 3 h with water, which
customto form
extractionThis mixture was extracted 3 times with EtOAc
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customdried under high vacuum

Sources & evidence

ORD record: ord-4aa5e2de5d954f6691d7583976d7f484
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881737B2

Reaction notes

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