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Diisopropylethylamine → N-(3,5-Bis-trifluoromethyl-benzyl)-6-chloro-4-(2-chloro-phenyl)-N-methyl-nicotinamide

HRID 1835340
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1835340
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[F:18][C:19]([F:34])([F:33])[C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[CH2:23][NH:24][CH3:25].C(N(C(C)C)C(C)C)C>CN(C)C=O.CN(C1C=CN=CC=1)C.ClCCl>[F:18][C:19]([F:33])([F:34])[C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[CH2:23][N:24]([CH3:25])[C:6](=[O:8])[C:5]1[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])=[CH:10][C:2]([Cl:1])=[N:3][CH:4]=1
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Komponenten

7

Edukt 3

HCID 81531DiisopropylethylamineHCID 10956204{[3,5-Bis(trifluoromethyl)phenyl]methyl}(methyl)amineHCID 235028066-Chloro-4-(2-chloro-phenyl)-nicotinic acid

Produkt 1

HCID 23502843N-(3,5-Bis-trifluoromethyl-benzyl)-6-chloro-4-(2-chloro-phenyl)-N-methyl-nicotinamideAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228
Dimethylformamide
Katalysator
HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a solution of 300 mg (1.12 mmol) 6-chloro-4-(2-chloro-phenyl)-nicotinic acid (Example 24, step e)) in 12 ml dichloromethane 0.15 ml (1.7 mmol) oxalyl chloride and one drop of N,N-dimethylformamide were added at 0° C. After completed addition the reaction mixture was allowed to warm to room temperature and stirred for 1 h. The reaction mixture was concentrated in vactio. The residue was redissolved in 6 ml dichloromethane and added dropwise to a solution of 432 mg (1.68 mmol) (3,5-bis-trifluoromethyl-benzyl)-methyl-amine, 0.39 ml (2.2 mmol) N-ethyldiisopropylamine and 7 mg (0.06 mmol) 4-(N,N-dimethylamino)pyridine in 6 ml dichloromethane at 0° C. After completed addition the reaction mixture was allowed to warm to room temperature and stirred over night. The reaction mixture was diluted with dichloromethane and washed with two portions of 1 M aqueous hydrochloric acid solution. The combined aqueous layers were extracted with dichloromethane. The combined organic extracts were washed with two portions of 1 M aqueous sodium hydroxide solution. The combined basic aqueous layers were extracted with dichloromethane. The combined organic extracts were dried with sodium sulfate and concentrated. Column chromatography afforded 475 mg (84%) of the title compound as a light yellow amorphous mass.

Aufarbeitung

  1. additionaddition the reaction mixture
  2. concentrationThe reaction mixture was concentrated in vactio
  3. dissolutionThe residue was redissolved in 6 ml dichloromethane
  4. additionaddition the reaction mixture
  5. temperatureto warm to room temperature
  6. stirringstirred over night
  7. washwashed with two portions of 1 M aqueous hydrochloric acid solution
  8. extractionThe combined aqueous layers were extracted with dichloromethane
  9. washThe combined organic extracts were washed with two portions of 1 M aqueous sodium hydroxide solution
  10. extractionThe combined basic aqueous layers were extracted with dichloromethane
  11. dry with materialThe combined organic extracts were dried with sodium sulfate
  12. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b6d3dda420d847e29203f0592b33feec
Quelldatensatz
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06770637B2

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