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Triethylamine → HCID 89714528, Verbindung

HRID 2273080
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2273080
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:18]3[C:17](=[O:19])[N:16]([CH3:20])[CH2:15][C:14]([CH3:22])([CH3:21])[O:13][C:12]=3[N:11]=[C:10]([N:23]3[CH2:29][CH:28]4[O:30][CH:25]([CH2:26][CH2:27]4)[CH2:24]3)[N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:39](Cl)([O:41]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:50][C:51]1[CH:56]=[C:55]([O:57][CH3:58])[CH:54]=[CH:53][N:52]=1>C(Cl)Cl.C(Cl)Cl.CO.CCCCC>[CH3:58][O:57][C:55]1[CH:54]=[CH:53][N:52]=[C:51]([NH:50][C:39]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[C:18]4[C:17](=[O:19])[N:16]([CH3:20])[CH2:15][C:14]([CH3:22])([CH3:21])[O:13][C:12]=4[N:11]=[C:10]([N:23]4[CH2:24][CH:25]5[O:30][CH:28]([CH2:27][CH2:26]5)[CH2:29]4)[N:9]=3)=[CH:6][CH:7]=2)=[O:41])[CH:56]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 108987152-Amino-4-MethoxypyridineHCID 89714608HCID 89714608, Verbindung

Produkt 1

HCID 89714528HCID 89714528, VerbindungAusbeute 29,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
2×
HCID 22051252HCID 22051252, VerbindungLösungsmittel

Versuchsvorschrift

210 mg (0.51 mmol) of 4-(4-aminophenyl)-6,8,8-trimethyl-2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-7,8-dihydro-6H-9-oxa-1,3,6-triazabenzocyclohepten-5-one and 314.5 mg (3 mmol) of triethylamine are added to 3 ml of DCM. This mixture is then added under nitrogen to a solution containing 152.2 mg (0.51 mmol) of triphosgene in 3 ml of DCM. The mixture is stirred at room temperature for 30 minutes, and 268.1 mg (2 mmol) of 2-amino-4-methoxypyridine are then added. This mixture is stirred for 2 hours at room temperature, extracted with DCM, washed once with water and then with saturated NaCl solution, and the organic phase is dried over Na2SO4. The resulting phase is filtered and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/MeOH mixture from (100/0 v/v) up to (100/4 v/v). The solid obtained is then taken up in a DCM/MeOH/pentane mixture, filtered off and dried to give 85 mg of 1-(4-methoxypyridin-2-yl)-3-{4-[6,8,8-trimethyl-2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-5-oxo-5,6,7,8-tetrahydro-9-oxa-1,3,6-triazabenzocyclohepten-4-yl]phenyl}urea.

Aufarbeitung

  1. additionThis mixture is then added under nitrogen to a solution
  2. stirringThis mixture is stirred for 2 hours at room temperature
  3. extractionextracted with DCM
  4. washwashed once with water
  5. dry with materialwith saturated NaCl solution, and the organic phase is dried over Na2SO4
  6. filtrationThe resulting phase is filtered
  7. customthe filtrate is evaporated under reduced pressure
  8. customThe residue is chromatographed on silica gel
  9. washeluting with a DCM/MeOH mixture from (100/0 v/v) up to (100/4 v/v)
  10. customThe solid obtained
  11. filtrationfiltered off
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2babbfc45fb94c59b95100f3e80aa0e3
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09120812B2

Notizen zur Reaktion

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