Methanol → Amuvatinib

HRID 1038963

Reaktionsgleichung

Reaktionsgleichung von HRID 1038963
[N:1]1([C:7]2[C:8]3[O:15][C:14]4[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=4[C:9]=3[N:10]=[CH:11][N:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[Cl-].[O:27]1[C:31]2[CH:32]=[CH:33][C:34]([CH2:36][NH:37][CH:38]=[S:39])=[CH:35][C:30]=2[O:29][CH2:28]1.CO>ClCCl>[O:27]1[C:31]2[CH:32]=[CH:33][C:34]([CH2:36][NH:37][C:38]([N:4]3[CH2:5][CH2:6][N:1]([C:7]4[C:8]5[O:15][C:14]6[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=6[C:9]=5[N:10]=[CH:11][N:12]=4)[CH2:2][CH2:3]3)=[S:39])=[CH:35][C:30]=2[O:29][CH2:28]1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 1049PyridineHCID 23685424-(Piperazin-1-yl)benzofuro[3,2-d]pyrimidineHCID 86601006N-Benzo[1,3]dioxol-5-ylmethyl-thioformamide chloride

Produkt 1

HCID 11282283Amuvatinib

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 4-piperazinobenzofurano[3,2-d]pyrimidine (200 mg, 0.79 mmol) and pyridine (0.5 mL, 7.9 mmol) in dichloromethane (20 mL) was added a solution of product 1c in dichloromethane (20 mL) and this was stirred overnight. Methanol was added to quench excess thiophosgene, and the residue after removal of solvent was purified by silica gel column chromatography eluting with 5% methanol/dichloromethane and further recrystallized from dichloromethane/hexane to give 150 mg (37%).

Aufarbeitung

  1. customto quench excess thiophosgene
  2. customthe residue after removal of solvent
  3. customwas purified by silica gel column chromatography
  4. washeluting with 5% methanol/dichloromethane
  5. customfurther recrystallized from dichloromethane/hexane
  6. customto give 150 mg (37%)

Quellen und Nachweise

ORD-Eintrag
ord-35b44185d2dc4457ac484f1158f245bc
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552018B2

Verknüpfte Notizen

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