Methanol → 1-(3-tert-Butyl-isoxazol-5-yl)-3-{2-[1-(2-dimethylamino-ethyl)-1H-indazol-5-yloxy]-5-fluoro-benzyl}-urea

HRID 909238

Reaktionsgleichung

Reaktionsgleichung von HRID 909238
[NH2:1][CH2:2][C:3]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:4]=1[O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[N:10]=[CH:9]2.[N+](C1C=CC([O:34][C:35](=O)[NH:36][C:37]2[O:41][N:40]=[C:39]([C:42]([CH3:45])([CH3:44])[CH3:43])[CH:38]=2)=CC=1)([O-])=O.CO>CN(C=O)C.ClCCl>[C:42]([C:39]1[CH:38]=[C:37]([NH:36][C:35]([NH:1][CH2:2][C:3]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:4]=2[O:5][C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[N:11]([CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[N:10]=[CH:9]3)=[O:34])[O:41][N:40]=1)([CH3:45])([CH3:43])[CH3:44]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 67408902(3-tert-Butyl-isoxazol-5-yl)-carbamic acid 4-nitrophenyl esterHCID 67411768{2-[5-(2-Aminomethyl-4-fluorophenoxy)-indazol-1-yl]-ethyl}-dimethylamine

Produkt 1

HCID 426422131-(3-tert-Butyl-isoxazol-5-yl)-3-{2-[1-(2-dimethylamino-ethyl)-1H-indazol-5-yloxy]-5-fluoro-benzyl}-ureaAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of {2-[5-(2-Aminomethyl-4-fluorophenoxy)-indazol-1-yl]-ethyl}-dimethylamine (0.020 g, 0.061 mmol) in DMF (1 mL) was treated with (3-tert-butylisoxazol-5-yl)-carbamic acid 4-nitrophenyl ester (0.020 g, 0.067 mmol) (prepared according to Example 136, Step E). The mixture stirred at room temperature for 18 hours under a N2 atmosphere. The reaction mixture was chromatographed eluting with dichloromethane/ether (10:1) and then 5% MeOH in dichloromethane to afford 5.3 mg of pale yellow oil (18% yield). MS (APCI+) m/z 495 (M+1) detected; 1H NMR (400 mHz, DMSO-D6) δ 10.14 (s, 1H), 7.98 (s, 1H), 7.74 (d, 1H), 7.22 (d, 1H), 7.16 (m, 2H), 7.08 (m, 1H), 6.88 (m, 2H), 5.93 (s, 1H), 4.48 (t, 2H), 4.35 (d, 2H), 2.70 (t, 2H), 2.17 (s, 6H), 1.23 (s, 9H).

Aufarbeitung

  1. customThe reaction mixture was chromatographed
  2. washeluting with dichloromethane/ether (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-d994bbb8e1724f60b65d89845134df42
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017641B2

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