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

Hydrochloric Acid → (2S)-2-(1-(3-chloropyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-N-(5-fluoropyridin-2-yl)-3-((S)-1-hydroxypropan-2-yloxy)propanamide

HRID 1098038
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1098038
Cl.[Si]([O:9][CH2:10][C@@H:11]([O:13][CH2:14][C@H:15]([O:26][C:27]1[N:32]=[CH:31][N:30]=[C:29]2[N:33]([C:36]3[C:41]([Cl:42])=[CH:40][CH:39]=[CH:38][N:37]=3)[N:34]=[CH:35][C:28]=12)[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][N:20]=1)=[O:17])[CH3:12])(C(C)(C)C)(C)C>C1COCC1>[Cl:42][C:41]1[C:36]([N:33]2[C:29]3=[N:30][CH:31]=[N:32][C:27]([O:26][C@@H:15]([CH2:14][O:13][C@@H:11]([CH3:12])[CH2:10][OH:9])[C:16]([NH:18][C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][N:20]=4)=[O:17])=[C:28]3[CH:35]=[N:34]2)=[N:37][CH:38]=[CH:39][CH:40]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 57504540(2S)-3-((S)-1-(tert-butyldimethylsilyloxy)propan-2-yloxy)-2-(1-(3-chloropyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-N-(5-fluoropyridin-2-yl)propanamide

Produkt 1

HCID 57504420(2S)-2-(1-(3-chloropyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-N-(5-fluoropyridin-2-yl)-3-((S)-1-hydroxypropan-2-yloxy)propanamideAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

HCl (4M in Dioxane) (0.530 mL, 2.12 mmol) was added to (2S)-3-((S)-1-(tert-butyldimethylsilyloxy)propan-2-yloxy)-2-(1-(3-chloropyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-N-(5-fluoropyridin-2-yl)propanamide (Intermediate AO3) (638 mg, 1.06 mmol) in THF (5 mL) at room temperature. The resulting solution was stirred for 20 minutes. The reaction mixture was evaporated and the residue partitioned between EtOAc (25 mL) and sat NaHCO3 (10 mL). The organic layer was dried (MgSO4) and evaporated. The crude product was purified by preparative chiral-HPLC on a Merck 50 mm 20 μm Chiralpak AS column, eluting isocratically with 30% EtOH in isohexane (modified with Et3N) as eluent to afford the product (397 mg, 77%). 1H NMR (400 MHz, CDCl3) δ1.16 (d, 3H), 2.73 (s, 1H), 3.51-3.68 (m, 2H), 3.69-3.78 (m, 1H), 4.12-4.28 (m, 2H), 6.06 (t, 1H), 7.42-7.50 (m, 2H), 7.99-8.03 (m, 1H), 8.13 (d, 1H), 8.21-8.26 (m, 1H), 8.47 (s, 1H), 8.60-8.65 (m, 2H), 9.09 (s, 1H); m/z (ESI+) (M+H)+=488.42; HPLC tR=1.75 min

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. customthe residue partitioned between EtOAc (25 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated
  5. customThe crude product was purified by preparative chiral-HPLC on a Merck 50 mm 20 μm Chiralpak AS column
  6. washeluting isocratically with 30% EtOH in isohexane (modified with Et3N) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-5fff1b2295244f28ac0e20c1c8e9e22e
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08143263B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion