1,2-Dichloroethane → 2-[(R)-2-(7-cyclopentylamino-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]-N-ethyl-acetamide

HRID 1876332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1876332
[CH:1]1([NH:6][C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:15]=2[NH:14][C:13]([C:16]2[S:17][CH2:18][C@@H:19]([CH2:21][C:22]([OH:24])=O)[N:20]=2)=[CH:12]3)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH2:26]([NH2:28])[CH3:27].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH:1]1([NH:6][C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:15]=2[NH:14][C:13]([C:16]2[S:17][CH2:18][C@@H:19]([CH2:21][C:22]([NH:28][CH2:26][CH3:27])=[O:24])[N:20]=2)=[CH:12]3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

8

Edukt 6

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 25197052[(R)-2-(7-cyclopentylamino-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]acetic acid

Produkt 1

HCID 595430782-[(R)-2-(7-cyclopentylamino-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]-N-ethyl-acetamideAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The compound (9 mg, 0.03 mmol) prepared in Example 42 was dissolved in N,N-dimethylformamide (1 ml). Ethylamine hydrochloride (3 mg, 0.03 mmol), EDC (8 mg, 0.04 mmol), HOBT (5 mg, 0.04 mmol) and triethylamine (8 mg, 0.08 mmol) were added thereto, and the mixture was stirred for 8 h at room temperature. After completion of the reaction, saturated sodium bicarbonate solution was added. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure, and concentrated. The residue was purified by column chromatography to give the title compound (4 mg, Yield 41%).

Aufarbeitung

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationThe filtrate was distilled under reduced pressure
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-59f9d7186faa4085a44a08f023f73a18
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309586B2

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