Cyanuric chloride → HCID 57546116, Verbindung

HRID 913930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 913930
[NH2:1][C:2](=O)[CH:3]([C:26]1[C:34]2[C:30](=[CH:31][N:32]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[N:33]=2)[CH:29]=[C:28]([Cl:43])[CH:27]=1)[O:4][CH2:5][C:6]1([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.N1C(Cl)=NC(Cl)=NC=1Cl>CN(C)C=O>[Cl:43][C:28]1[CH:27]=[C:26]([CH:3]([C:2]#[N:1])[O:4][CH2:5][C:6]2([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[C:34]2[C:30](=[CH:31][N:32]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[N:33]=2)[CH:29]=1

Komponenten

4

Edukt 2

HCID 7954Cyanuric chlorideHCID 57546167tert-butyl 4-((2-amino-1-(5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)-2-oxoethoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate

Produkt 1

HCID 57546116HCID 57546116, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 4-((2-amino-1-(5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)-2-oxoethoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate (64 mg, 0.099 mmol) in dimethylformamide (0.7 mL) at 0° C. was added cyanuric chloride (18.2 mg, 0.10 mmol). The ice bath was removed and stirring continued for 5 h. The reaction was diluted with diethyl ether and quenched by addition of water. After stirring for 10 min, the ethereal was washed with water (2×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography (18%→25% ethyl acetate/n-hexane) gave 31 mg (50%) as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ0 8.08 (s, 1H), 7.68 (d, J=1.2 Hz, 1H), 7.29 (dd, J=8.6, 5.2 Hz, 2H), 7.24 (s, 1H), 7.00 (dd, J=8.9, 8.5 Hz, 2H), 5.71 (s, 1H), 5.69 (d, J=10.7 Hz, 1H), 5.64 (d, J=10.7 Hz, 1H), 3.76 (m, 3H), 3.61 (t, J=8.2 Hz, 2H), 3.58 (d, J=8.9 Hz, 1H), 3.03 (m, 2H), 2.14 (m, 2H), 1.90 (m, 2H), 1.43 (s, 9H), 0.92 (m, 2H), −0.03 (s, 9H); 13C NMR (126 MHz, CDCl3) δ ppm 161.5 (d, J=246 Hz), 155.0, 144.3, 137.6, 128.9 (d, J=8.6 Hz), 127.6, 125.9, 124.4, 122.92, 122.87, 121.0, 116.6, 115.4(d, J=21 Hz), 82.1, 79.6, 78.6, 68.0, 66.5, 41.2, 40.0 (br), 32.0, 28.5, 17.9, −1.3. Mass spec.: 629.35 (MH)+

Aufarbeitung

  1. customThe ice bath was removed
  2. additionThe reaction was diluted with diethyl ether
  3. customquenched by addition of water
  4. stirringAfter stirring for 10 min
  5. washthe ethereal was washed with water (2×)
  6. dry with materialbrine, dried over magnesium sulfate
  7. concentrationconcentrated
  8. customColumn chromatography (18%→25% ethyl acetate/n-hexane) gave 31 mg (50%) as a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-2c2403a54aa64406915db81fee39111c
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026257B2

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