Reaktionsgleichung
[Cl:1][C:2]1[C:3]2[C:10](I)=[CH:9][N:8]([C@H:12]3[CH2:17][CH2:16][C@H:15]([N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)[CH2:14][CH2:13]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:25][O:26][C:27]1[CH:28]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:30]=[CH:31][C:32]=1[O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.ClC1C2C(C3C=CC(OC4C=CC=CC=4)=C(C=3)C#N)=CN([C@H]3CC[C@H](N4CCN(C)CC4)CC3)C=2N=CN=1.CO[C@@H]1[C@@H](C(OC)=O)[C@@H]2[C@@H](CN3[C@H](C2)C2NC4C=C(OC)C=CC=4C=2CC3)C[C@H]1OC(C1C=C(OC)C(OC)=C(OC)C=1)=O>C(#N)C>[Cl:1][C:2]1[C:3]2[C:10]([C:29]3[CH:30]=[CH:31][C:32]([O:33][C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)=[C:27]([O:26][CH3:25])[CH:28]=3)=[CH:9][N:8]([C@H:12]3[CH2:17][CH2:16][C@H:15]([N:18]4[CH2:23][CH2:22][NH:21][CH2:24][CH:19]4[CH3:20])[CH2:14][CH2:13]3)[C:4]=2[N:5]=[CH:6][N:7]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
The title compound (223 mg, 64%) was prepared from trans-4-chloro-5-iodo-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidine (300 mg, 0.655 mmol) and 2-(3-methoxy-4-phenoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (235 mg, 0.727 mmol) in a similar manner to that described for the preparation of trans-5-(4-chloro-7-(4-(4-methylpiperazino)cyclohexyl)-7H-pyrrolo[2,3-d ]pyrimidin-5-yl)-2-phenoxybenzonitrile: 1H NMR (DMSO-d6, 400 MHz) δ 8.67(s, 1H), 8.04(s, 1H), 7.32(m, 4H), 7.12(d, 1H), 7.08(d, 1H), 6.88(d, 2H), 4.71(m, 1H), 3.80(s, 3H), 2.2-2.6(m, 9H), 2.15(s, 3H), 1.9-2.1 (m, 6H), 1.49(m, 2H); MS MH+532.4; RP-HPLC (Hypersil HS, 5 μm, 100 Å 4.6×250 mm; 25%-100% acetonitrile—0.05 M ammonium acetate over 10 min, 1 ml/min) tr 9.58 min.
Quellen und Nachweise
- ORD-Eintrag
- ord-224a4e47845b40758108a3815bdf011a
- Quelldatensatz
- uspto-grants-2004_03
- Patentnummer
- US06713474B2
Verknüpfte Notizen
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