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Sodium Hydroxide → 11-Bromo-6-chloro-15-oxa-2,4,8,25-tetraazatetracyclo[17.3.1.1(3,7).1(10,14)]pentacosa-1(23),3(25),4,6,10(24),11,13,19,21-nonaene

HRID 1614971
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Reaktionsgleichung

Reaktionsgleichung von HRID 1614971
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH2:9][NH:10][C:11]1[C:16]([Cl:17])=[CH:15][N:14]=[C:13]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][CH2:26][CH2:27]Br)[CH:20]=2)[N:12]=1.[OH-].[Na+]>O1CCCC1.O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Br:1][C:2]1[C:3]2[CH2:9][NH:10][C:11]3[N:12]=[C:13]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([CH:20]=4)[CH2:25][CH2:26][CH2:27][O:8][C:5]([CH:4]=2)=[CH:6][CH:7]=1)[N:14]=[CH:15][C:16]=3[Cl:17]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 14798Sodium HydroxideHCID 584679264-Bromo-3-{[(2-{[3-(3-bromopropyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]methyl}phenol

Produkt 1

HCID 4686474711-Bromo-6-chloro-15-oxa-2,4,8,25-tetraazatetracyclo[17.3.1.1(3,7).1(10,14)]pentacosa-1(23),3(25),4,6,10(24),11,13,19,21-nonaeneAusbeute 35,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 66133Benzyl triethylammonium chlorideKatalysator
HCID 962WaterLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

To a solution of 4-bromo-3-{[(2-{[3-(3-bromopropyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]methyl}phenol (1.00 g, 1.90 mmol) in tetrahydrofuran (9.0 mL) was added a solution of sodium hydroxide in water (18 mL, 4.0 M). The resultant solution was then treated with benzyltriethylammonium chloride (30.0 mg, 0.13 mmol) and heated at 35° C. for 40 hours. The reaction mixture could not be purified by silica gel column chromatography or prep-HPLC. However, after cooling, THF and alkaline NaOH layers could be separated. THF layer was washed with brine and concentrated to give a light yellow solid residue, which was triturated with MeOH/EtOAc (90:10). After vacuum filtration, the cake was washed with MeOH to provide the desired pure product (300 mg, 35%) as an off-white powder. LCMS for C20H18BrClN4O (M+H)+: m/z=444.9, 446.9. 1H NMR (400 MHz, DMSO-d6): δ 8.76 (s, 1H), 7.86 (s, 1H), 7.50 (s, 1H), 7.31 (d, J=8.8 Hz, 1H), 7.27 (m, 1H), 7.16 (m, 1H), 7.04 (m, 2H), 6.68 (m, 1H), 6.20 (m, 1H), 4.23 (m, 2H), 4.02 (t, 2H), 3.15 (m, 1H), 2.65 (m, 2H), 1.96 (m, 2H).

Aufarbeitung

  1. customThe reaction mixture could not be purified by silica gel column chromatography
  2. temperatureHowever, after cooling
  3. customTHF and alkaline NaOH layers could be separated
  4. washTHF layer was washed with brine
  5. concentrationconcentrated
  6. customto give a light yellow solid residue, which
  7. customwas triturated with MeOH/EtOAc (90:10)
  8. filtrationAfter vacuum filtration
  9. washthe cake was washed with MeOH

Quellen und Nachweise

ORD-Eintrag
ord-c27a294af5b54e56b22dbc055e0c7d9e
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08765727B2

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