Hydrochloric Acid → 6-Chloro-16-oxa-2,4,8,26-tetraazatetracyclo[18.3.1.1(3,7).1(11,15)]hexacosa-1(24),3(26),4,6,11(25),12,14,20,22-nonaene

HRID 1614963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1614963
Br[CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:17]=[C:16]([NH:18][CH2:19][CH2:20][C:21]3[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=3)[C:15]([Cl:28])=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1.[OH-].[Na+].Cl>O1CCCC1.O>[Cl:28][C:15]1[CH:14]=[N:13][C:12]2[NH:11][C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([CH:6]=3)[CH2:4][CH2:3][CH2:2][O:27][C:23]3[CH:22]=[C:21]([CH2:20][CH2:19][NH:18][C:16]=1[N:17]=2)[CH:26]=[CH:25][CH:24]=3

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 584678483-{2-[(2-{[3-(3-Bromopropyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]ethyl}phenol

Produkt 1

HCID 468647456-Chloro-16-oxa-2,4,8,26-tetraazatetracyclo[18.3.1.1(3,7).1(11,15)]hexacosa-1(24),3(26),4,6,11(25),12,14,20,22-nonaeneAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-{2-[(2-{[3-(3-bromopropyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]ethyl}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 twice. The combined organic layers were dried over Na2SO4, filtered, and concentrated to give a residue, which was purified by silica gel column chromatography to give the desired product as a white powder (4.0 mg, 10%). LCMS for C21H22ClN4O (M+H)+: m/z=381.0. 1H NMR (400 MHz, CD3OD): δ 7.95 (s, 1H), 7.90 (s, 1H), 7.30 (m, 3H), 7.12 (t, J=7.4 Hz, 1H), 6.94 (m, 1H), 6.65 (m, 2H), 3.70 (t, J=7.6 Hz, 2H), 3.48 (t, J=6.8 Hz, 2H), 2.80 (m, 2H), 2.72 (m, 2H), 2.10 (m, 2H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-718ec02163de452a94eebc2970e36c8e
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765727B2

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