Ammonium Chloride → 2-(4-(2-(Trifluoromethyl)phenoxy)piperidin-1-yl)thiazole-5-carboxamide

HRID 561200Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561200
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[S:13][C:14]([C:17](O)=[O:18])=[CH:15][N:16]=2)[CH2:8][CH2:7]1.C1C=CC2N(O)N=[N:32]C=2C=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH4+].[Cl-].CCN(C(C)C)C(C)C>CN(C=O)C>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[S:13][C:14]([C:17]([NH2:32])=[O:18])=[CH:15][N:16]=2)[CH2:10][CH2:11]1

Komponenten

7

Edukt 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 666968024-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl-1,3-thiazole-5-carboxylic acid

Produkt 1

HCID 468806672-(4-(2-(Trifluoromethyl)phenoxy)piperidin-1-yl)thiazole-5-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-1,3-thiazole-5-carboxylic acid (14.5 g, 39 mmol), HOBt (5.3 g, 39 mmol)), HATU (23.7 g, 62 mmol) and NH4Cl (6.3 g, 117 mmol) in DMF (200 mL) at room temperature was added Hünig's base (34 mL, 195 mmol) over about 15 min. The mixture was stirred at room temperature overnight. After dilution with water, the mixture was extracted twice with EtOAc. The EtOAc extracts were combined, washed with 0.5 N NaOH (2×), diluted brine (1×), dried (Na2SO4) and concentrated. The residue was triturated with Et2O/hexanes (1:1) to give the title compound as a pale yellow solid. 1H NMR (500 MHz, acetone-d6): δ7.79 (s, 1H), 7.67-7.61 (m, 2H), 7.38 (d, 1H), 7.12 (t, 1H), 5.02 (s, 1H), 3.76 (t, 2H), 3.71-3.67 (m, 2H), 2.16 (t, 2H), 2.00-1.94 (m, 2H).

Aufarbeitung

  1. extractionAfter dilution with water, the mixture was extracted twice with EtOAc
  2. washwashed with 0.5 N NaOH (2×), diluted brine (1×)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was triturated with Et2O/hexanes (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-4be4b7674a2e4ecebaf94970fa96e13c
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063224B2

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