StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Sodium Bicarbonate → HCID 136344271, Verbindung

HRID 1442993
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1442993
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=3)=[N:14][CH:15]=[N:16]2)=[C:11]([O:28][CH2:29][C@H:30]2[CH2:34][CH2:33][CH2:32][N:31]2C(OC(C)(C)C)=O)[CH:10]=1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O>[Cl:27][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[F:26])[NH:19][C:13]1[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[CH:10][C:11]=2[O:28][CH2:29][C@H:30]2[CH2:34][CH2:33][CH2:32][NH:31]2)[N:16]=[CH:15][N:14]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 86607803tert-butyl (2R)-2-[({7-(benzyloxy)-4-[3-chloro-4-fluoroanilino]quinazolin-5-yl}oxy)methyl]pyrrolidine-1-carboxylate

Produkt 1

HCID 136344271HCID 136344271, VerbindungAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

tert-Butyl (2R)-2-[({7-(benzyloxy)-4-[3-chloro-4-fluoroanilino]quinazolin-5-yl}oxy)methyl]pyrrolidine-1-carboxylate (1.5 g) was taken up in trifluoroacetic acid (15 ml) and the solution was heated at 70° C. for 18 hours. The solution was cooled to room temperature and then concentrated in vacuo to leave a brown residue. Saturated aqueous sodium hydrogen carbonate was added to the residue and the aqueous mixture was extracted with ethyl acetate. The layers were separated and the organic layer was dried (MgSO4) and concentrated in vacuo to leave a brown oil. Purification by flash chromatography, using 5:1:84 methanol:7N ammonia in methanol:DCM→20:1:79 methanol:7N ammonia in methanol:DCM as eluent, followed by trituration with ether gave 4-[3-chloro-4-fluoro-anilino]-5-[(2R)-pyrrolidin-2-ylmethoxy]quinazolin-7-ol as an off-white solid (200 mg, 20%); NMR Spectrum (DMSO-d6) 10.40 (brs, 1H), 8.40 (s, 1H), 8.15 (m, 1H), 7.95 (m, 1H), 7.40 (m, 1H), 6.75 (m, 2H), 4.30 (m, 1H), 4.05 (m, 1H), 3.60-3.50 (m, 1H), 3.0-2.80 (m, 2H), 1.95-1.80 (m, 1H), 1.75-1.65 (m, 2H), 1.50-1.40 (m, 1H); Mass spectrum MH+ 391.

Aufarbeitung

  1. temperatureThe solution was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customto leave a brown residue
  4. extractionthe aqueous mixture was extracted with ethyl acetate
  5. customThe layers were separated
  6. dry with materialthe organic layer was dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto leave a brown oil
  9. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-77042358e09d46eda2a5015df3751ded
Quelldatensatz
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07659279B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion