Diisopropylethylamine → (+/-)-1-[3-(Benzhydrylidene-amino)-4-cyano-benzyl]-4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-6-oxo-piperazine-2-carboxylic acid methyl ester

HRID 1432942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432942
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][NH:9][CH2:8][C:7](=[O:11])[N:6]1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[C:15]([N:21]=[C:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:14]=1)=[O:4].CCN(C(C)C)C(C)C.[Cl:44][C:45]1[CH:46]=[CH:47][C:48]2[CH:52]=[C:51]([S:53](Cl)(=[O:55])=[O:54])[S:50][C:49]=2[CH:57]=1>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][N:9]([S:53]([C:51]2[S:50][C:49]3[CH:57]=[C:45]([Cl:44])[CH:46]=[CH:47][C:48]=3[CH:52]=2)(=[O:55])=[O:54])[CH2:8][C:7](=[O:11])[N:6]1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[C:15]([N:21]=[C:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:14]=1)=[O:4]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 151586416-Chlorobenzo[b]thiophene-2-sulfonyl chlorideHCID 54153171(+/-)-1-[3-(Benzhydrylidene-amino)-4-cyano-benzyl]-6-oxo-piperazine-2-carboxylic acid methyl ester

Produkt 1

HCID 54128933(+/-)-1-[3-(Benzhydrylidene-amino)-4-cyano-benzyl]-4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-6-oxo-piperazine-2-carboxylic acid methyl esterAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution containing (±)-1-[3-(benzhydrylidene-amino)-4-cyano-benzyl]-6-oxo-piperazine-2-carboxylic acid methyl ester (55 mg, 0.12 mmol) in CH2Cl2 (1 mL) is cooled to 0° C. DIPEA (24 mg, 0.18 mmol) is then added followed by the addition of 6-chloro-benzo[b]thiophene-2-sulfonyl chloride (32 mg, 0.12 mmol), EXAMPLE 1. The reaction mixture is warmed to ambient temperature. After 16 h, the reaction mixture is absorbed directly onto silica gel and chromatographed (CH2Cl2 to 2% MeOH/CH2Cl2) to provide 60 mg (73%) of the title compound. 1H NMR (300 MHz, CDCl3) δ2.77 (dd, J=12.3, 3.4 Hz, 1H), 3.50-3.72 (m, 3H), 3.79 (s, 3H), 4.15 (dd, J=12.3, 1.4 Hz, 1H), 4.24 (d, J=16.9 Hz, 1H), 5.41 (d, J=15.3 Hz, 1H), 6.50 (s, 1H), 6.76 (dd, J=7.9, 1.4 Hz, 1H), 7.11-7.86 (m, 15H) ppm; MS (ISP loop): m/z 683 (M+H).

Aufarbeitung

  1. temperatureThe reaction mixture is warmed to ambient temperature
  2. customthe reaction mixture is absorbed directly onto silica gel
  3. customchromatographed (CH2Cl2 to 2% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-e9f546057c7043dd956fb42a25d02bef
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612075B2

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