Triethylamine → HCID 59565293, Verbindung

HRID 1962885Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1962885
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:18][CH3:19])[C:15]([OH:17])=O)=[C:8]([F:20])[C:7]=2[CH3:21])#[CH:2].CN(C(ON1N=[N:37][C:32]2[CH:33]=CC=C[C:31]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:44]CN(CC)CC.[NH4+].[Cl-]>CC#N.C(N)(C)(C)C>[C:32]([NH:37][C:15](=[O:17])[CH:14]([O:13][C:9]1[CH:10]=[C:11]2[C:6](=[C:7]([CH3:21])[C:8]=1[F:20])[N:5]=[CH:4][C:3]([C:1]#[CH:2])=[CH:12]2)[S:18][CH3:19])([CH3:44])([CH3:33])[CH3:31]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86647256HCID 86647256, Verbindung

Produkt 1

HCID 59565293HCID 59565293, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6385Tert-ButylamineLösungsmittel

Versuchsvorschrift

To a mixture containing (3-ethynyl-7-fluoro-8-methyl-quinolin-6-yloxy)-methylsulfanyl-acetic acid (250 mg) from Step 8, aza-HOBT (116 mg), TBTU (273 mg) and Et3N (0.32 ml) in CH3CN (12 ml), tert-butyl amine was added at room temperature, under a nitrogen atmosphere. The resulting brown suspension was stirred 1 hour at room temperature then poured into aqueous NH4Cl solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulphate anhydrous, filtered and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate) to give N-tert-butyl-2-(3-ethynyl-7-fluoro-8-methyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide (201 mg) as white solid. 1H NMR (CDCl3) δ ppm: 8.88 (1H, d); 8.17 1H, d); 7.17 (1H, d); 6.64 (1H, br s); 5.59 (1H, s); 3.27 (1H, s); 2.69 (3H, d); 2.18 (3H, s); 1.44 (9H, s).

Aufarbeitung

  1. additionwas added at room temperature, under a nitrogen atmosphere
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulphate anhydrous
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-6f4b6c90448d43878ad4cb0bda834a24
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415272B2

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