Sodium Iodide → [3-(2-Methanesulfonyl-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl]-[5-(2-methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amine

HRID 472530Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 472530
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:15]2[N:16]=[C:17]([NH:19][C:20]3[CH:30]=[CH:29][C:23]4[CH2:24][CH2:25][NH:26][CH2:27][CH2:28][C:22]=4[CH:21]=3)[N:18]=[C:14]2[CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:38][CH2:39][S:40]([CH3:43])(=[O:42])=[O:41].[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:43][S:40]([CH2:39][CH2:38][N:26]1[CH2:27][CH2:28][C:22]2[CH:21]=[C:20]([NH:19][C:17]3[N:18]=[C:14]4[CH:13]=[CH:12][CH:11]=[C:10]([C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=5[CH2:3][O:2][CH3:1])[N:15]4[N:16]=3)[CH:30]=[CH:29][C:23]=2[CH2:24][CH2:25]1)(=[O:42])=[O:41]

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 3035331-Chloro-2-methanesulfonylethaneHCID 59612550[5-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)-amine

Produkt 1

HCID 59612426[3-(2-Methanesulfonyl-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl]-[5-(2-methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amineAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of [5-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-amine (0.100 g, 0.250 mmol) in N,N-dimethylformamide (3 mL) was added potassium carbonate (0.103 g, 0.751 mmol), 1-chloro-2-methanesulfonyl-ethane (0.053545 g, 0.37548 mmol), followed by sodium iodide (0.037 g, 0.250 mmol) and the reaction was heated at 60° C. overnight then cooled to room temperature. The reaction was diluted with ethyl acetate, washed with water several times, washed with brine, dried over sodium sulfate, and concentrated. Product was isolated as a pale yellow foam (0.062 g, 49%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.64 (d, J=7.7 Hz, 1H), 7.59-7.42 (m, 5H), 7.31-7.29 (m, 1H), 7.24-7.20 (m, 1H), 7.08 (s, 1H), 6.98 (d, J=8.1 Hz, 1H), 6.92-6.88 (m, 1H), 4.35 (br s, 2H), 3.20-3.14 (m, 5H), 3.06 (s, 3H), 3.01 (t, J=6.1 Hz, 2H), 2.87-2.82 (m, 4H), 2.71-2.64 (m, 4H). MS=506 (MH)+.

Aufarbeitung

  1. temperaturethen cooled to room temperature
  2. washwashed with water several times
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8ee77b84be1a428ba3240477f1bec2ec
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633173B2

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