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1,1'-Carbonyldiimidazole → HCID 60198533, Verbindung

HRID 2279507
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2279507
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:12][C:13]([N:15]2[CH2:24][C:23]([F:26])([F:25])[C:22]3[CH:21]=[N:20][C:19]([NH:27][CH:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[N:18][C:17]=3[CH2:16]2)=[O:14])[CH2:9]OC)=[CH:4][C:3]=1F.[Cl:35]C1C=CC([C@H](N)COC)=CC=1F.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.FC1(F)C2C=NC(NC3CCOCC3)=NC=2CNC1>O.C(Cl)Cl>[Cl:35][C:3]1[CH:4]=[C:5]([C@H:8]([NH:12][C:13]([N:15]2[CH2:24][C:23]([F:25])([F:26])[C:22]3[CH:21]=[N:20][C:19]([NH:27][CH:28]4[CH2:29][CH2:30][O:31][CH2:32][CH2:33]4)=[N:18][C:17]=3[CH2:16]2)=[O:14])[CH3:9])[CH:6]=[CH:7][C:2]=1[Cl:1]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 682631,1'-CarbonyldiimidazoleHCID 86705500HCID 86705500, VerbindungHCID 86705502HCID 86705502, VerbindungHCID 86705503HCID 86705503, Verbindung

Produkt 1

HCID 60198533HCID 60198533, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(S)—N-(1-(4-chloro-3-fluorophenyl)-2-methoxyethyl)-5,5-difluoro-2-(tetrahydro-2H-pyran-4-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide (I-51) To a solution of 197 (0.0854 g, 0.293 mmol) and DCM (5 mL) was added sequentially TEA (0.123 mL, 0.880 mmol) and CDI (0.0476 g, 0.293 mmol) and the solution was stirred at RT for 30 min. To the solution was added dropwise a solution of TEA (0.123 mL, 0.880 mmol), 208 (0.090 g, 0.293 mmol) and DCM (5 mL). The reaction was stirred for 18 h then poured into water and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with 2% MeOH/DCM to afford 0.060 g (40.9%) of I-51: MS m/z (APCI-pos) M+1=499.

Aufarbeitung

  1. stirringThe reaction was stirred for 18 h
  2. extractionextracted with DCM
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by SiO2 chromatography
  7. washeluting with 2% MeOH/DCM
  8. customto afford 0.060 g (40.9%) of I-51

Quellen und Nachweise

ORD-Eintrag
ord-7c1eb5642099408dbe4e86aed027ccf2
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09133187B2

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