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Hydrochloric Acid → 21-Chloro-10-oxa-2,19,23,24-tetrazatetracyclo[18.3.1.13,7.111,15]hexacosa-1(23),3,5,7(26),11,13,15(25),20(24),21-nonaene

HRID 1614966
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1614966
Br[CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[C:15]([NH:17][CH2:18][CH2:19][CH2:20][C:21]3[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=3)[C:14]([Cl:28])=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1.[OH-].[Na+].Cl>O1CCCC1.O>[Cl:28][C:14]1[CH:13]=[N:12][C:11]2=[N:16][C:15]=1[NH:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:22]=[C:23]([O:27][CH2:2][CH2:3][C:4]3[CH:5]=[C:6]([NH:10]2)[CH:7]=[CH:8][CH:9]=3)[CH:24]=[CH:25][CH:26]=1
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Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58467888HCID 58467888, Verbindung

Produkt 1

HCID 4686474621-Chloro-10-oxa-2,19,23,24-tetrazatetracyclo[18.3.1.13,7.111,15]hexacosa-1(23),3,5,7(26),11,13,15(25),20(24),21-nonaeneAusbeute 11 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-{3-[(2-{[3-(2-bromoethyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]propyl}phenol (50.0 mg, 0.108 mmol) in tetrahydrofuran (1.0 mL) was added a solution of sodium hydroxide in water (1.0 mL, 1.0 M). The resultant solution was stirred at rt for 60 hours until the reaction was complete. The reaction mixture was neutralized with HCl (3 M aqueous solution) to pH=7. The aqueous layer was extracted with EtOAc three times. The combined organic layers were dried over Na2SO4, filtered, and concentrated to give the crude, which was purified by silica gel column chromatography to give the desired product as a white powder (4.5 mg, 11%). LCMS for C21H22ClN4O (M+H)+: m/z=381.0. 1H NMR (400 MHz, CD3OD): δ 7.98 (s, 1H), 7.92 (s, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.40 (m, 1H), 7.06 (m, 1H), 6.97 (s, 1H), 6.70 (d, J=2.4 Hz, 1H), 6.62 (m, 2H), 3.60 (m, 4H), 3.20 (m, 2H), 2.68 (t, J=7.6 Hz, 2H), 2.02 (t, J=7.6 Hz, 2H).

Aufarbeitung

  1. extractionThe aqueous layer was extracted with EtOAc three times
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude, which
  6. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fed1cec749944667b9b441390aa4c4a5
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08765727B2

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