Ammonium Hydroxide → 5-{4-amino-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-2-phenoxybenzonitrile bisacetate

HRID 51570

Reaktionsgleichung

Reaktionsgleichung von HRID 51570
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:15]([CH:18]=3)[C:16]#[N:17])=[CH:9][N:8]([C@H:26]3[CH2:31][CH2:30][C@H:29]([N:32]4[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]4)[CH2:28][CH2:27]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[OH-:39].[NH4+:40]>O1CCOCC1>[C:20]([OH:39])(=[O:19])[CH3:25].[C:14]([OH:19])(=[O:39])[CH3:13].[NH2:40][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:15]([CH:18]=3)[C:16]#[N:17])=[CH:9][N:8]([CH:26]3[CH2:31][CH2:30][CH:29]([N:32]4[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]4)[CH2:28][CH2:27]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Komponenten

4

Edukt 2

HCID 14923Ammonium HydroxideHCID 178480939HCID 178480939, Verbindung

Produkt 1

HCID 865890125-{4-amino-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-2-phenoxybenzonitrile bisacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of trans-5-(4-chloro-7-(4-(4-methylpiperazino)cyclohexyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-phenoxybenzonitrile (150 mg) in 1,4-dioxane (25 mL) and 30% aqueous ammonium hydroxide (25 mL) was heated at 120° C. in a sealed tube for 18 hours then cooled and evaporated under reduced pressure. The residue was purified by preparative RP-HPLC to give 5-{4-amino-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-2-phenoxybenzonitrile bisacetate: 1H NMR (DMSO-d6, 400 MHz) δ 8.14(s, 1H), 7.91(s, 1H), 7.70(d, 1H), 7.55(s, 1H), 7.48(t, 2H), 7.27(t, 1H), 7.20(d, 2H), 7.06(d, 1H), 6.27(bs, 2H), 4.55 (m, 1H), 2.53 m, 4H), 2.36(m, 5H), 2.17 (s, 3H), 2.0(m, 6H), 1.96(s, 6H); MS MH+508.3; RP-HPLC (Hypersil HS, 5 μm, 100 A, 4.6×250 mm; 25%-100% acetonitrile—0.05 M ammonium acetate over 10 min, 1 ml/min) tr 7.27 min.

Aufarbeitung

  1. temperaturethen cooled
  2. customevaporated under reduced pressure
  3. customThe residue was purified by preparative RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-0b6702c93e214fc7927f6b78e6c33a75
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713474B2

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