Triethylamine → 2-Trifluoroacetyl-1,2,3,4-tetrahydro-isoquinoline-7-sulfonic acid dimethylamide

HRID 586185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 586185
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([S:15](Cl)(=[O:17])=[O:16])=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].Cl.[CH3:22][NH:23][CH3:24].C(N(CC)CC)C>O1CCOCC1>[CH3:22][N:23]([CH3:24])[S:15]([C:9]1[CH:8]=[C:7]2[C:12]([CH2:13][CH2:14][N:5]([C:3](=[O:4])[C:2]([F:20])([F:19])[F:1])[CH2:6]2)=[CH:11][CH:10]=1)(=[O:17])=[O:16]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 113249022-(Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chloride

Produkt 1

HCID 571630872-Trifluoroacetyl-1,2,3,4-tetrahydro-isoquinoline-7-sulfonic acid dimethylamideAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 2-trifluoroacetyl-1,2,3,4-tetrahydro-isoquinoline-7-sulfonyl chloride (400 mg, 1.22 mmol, J. Med. Chem. 1980, 23, 837), dimethylamine hydrochloride (150 mg, 1.83 mmol), and triethylamine (0.50 mL, 3.66 mmol) in dioxane (10 mL) was refluxed with stirring for 30 min, cooled to room temperature, concentrated, and purified by flash column chromatography (10→50% ethyl acetate/hexanes) to give 337 mg (82%) of the title compound of Example 247, Step A as a yellow oil. 1H NMR (CDCl3, 300 MHz, 9:5 mixture of rotamers) δ 7.67-7.52 (c, 2H), 7.36 (t, 1H), 4.87 (s, 1.3H), 4.81 (s, 0.7H), 3.96-3.86 (c, 2H), 3.08-3.02 (c, 2H), 2.72 (s, 6H); MS (TS) 337 (MH+).

Aufarbeitung

  1. temperaturewas refluxed
  2. concentrationconcentrated
  3. custompurified by flash column chromatography (10→50% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b03ae671d08a42b5afb5df0fac5dc5a1
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06936600B2

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