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Water → 3-Methyl-pyridine-2-carboxylic acid [1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropylmethyl]-amide

HRID 578859
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 578859
[Cl:1][C:2]1[C:3]([C:12]2([CH2:15][NH2:16])[CH2:14][CH2:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(N(CC)CC)C.[CH3:24][C:25]1[C:26]([C:31](Cl)=[O:32])=[N:27][CH:28]=[CH:29][CH:30]=1.O>ClCCl>[Cl:1][C:2]1[C:3]([C:12]2([CH2:15][NH:16][C:31]([C:26]3[C:25]([CH3:24])=[CH:30][CH:29]=[CH:28][N:27]=3)=[O:32])[CH2:14][CH2:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 204875083-Methylpyridine-2-carbonyl chlorideHCID 71559141(1-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)cyclopropyl)methanamine

Produkt 1

HCID 715588383-Methyl-pyridine-2-carboxylic acid [1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropylmethyl]-amideAusbeute 39,2 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

180 mg of C-[1-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropyl]-methylamine (step 1) was dissolved in 5 ml of dichloromethane and cooled to 0° C. Then 145 mg of triethylamine was added, followed by dropwise addition of a solution of 112 mg of 3-methyl-pyridine-2-carbonyl chloride in 1 ml of dichloromethane. The reaction mixture was stirred at ambient temperature for 2 hours. Then 6 ml of water were added, the resulting phases were separated and the organic phase was washed with aqueous 2N sodium hydroxide solution, then with 1N aqueous hydrochloric acid and brine, dried over sodium sulfate, filtered and concentrated. Thus, 282 mg of crude material was obtained as a brown sticky solid. This residue was purified by chromatography on silica gel, with cyclohexane/ethyl acetate (1:1) as a eluent. Thus, 104 mg of 3-methyl-pyridine-2-carboxylic acid [1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropylmethyl]-amide was obtained as a sticky oil. 1H-NMR (CDCl3): 8.64 ppm (s, 1H), 8.35 ppm (m, 2H), 7.90 ppm (s, 1H), 7.53 ppm (m, 1H), 7.27 ppm (m, 1H), 3.74 (d, 2H), 2.60 ppm (s, 3H), 1.16 ppm (m, 2H), 1.12 ppm (m, 2H).

Aufarbeitung

  1. customthe resulting phases were separated
  2. washthe organic phase was washed with aqueous 2N sodium hydroxide solution
  3. dry with materialwith 1N aqueous hydrochloric acid and brine, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThus, 282 mg of crude material was obtained as a brown sticky solid
  7. customThis residue was purified by chromatography on silica gel, with cyclohexane/ethyl acetate (1:1) as a eluent

Quellen und Nachweise

ORD-Eintrag
ord-764959b17c004fffbffc7c29b64d1048
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09040708B2

Notizen zur Reaktion

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