Oxalyl chloride → N-(5-tert-butyl-2-methoxy-3-(methylsulfonamido)phenyl)-2-(4-(2-morpholinopyrimidin-4-yloxy)naphthalen-1-yl)-2-oxoacetamide

HRID 2353543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2353543
[N:1]1([C:7]2[N:12]=[C:11]([O:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]([C:24](=[O:28])[C:25]([OH:27])=O)=[CH:16][CH:15]=3)[CH:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.[NH2:35][C:36]1[C:37]([O:51][CH3:52])=[C:38]([NH:46][S:47]([CH3:50])(=[O:49])=[O:48])[CH:39]=[C:40]([C:42]([CH3:45])([CH3:44])[CH3:43])[CH:41]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[C:42]([C:40]1[CH:39]=[C:38]([NH:46][S:47]([CH3:50])(=[O:49])=[O:48])[C:37]([O:51][CH3:52])=[C:36]([NH:35][C:25](=[O:27])[C:24]([C:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]([O:13][C:11]3[CH:10]=[CH:9][N:8]=[C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)[N:12]=3)=[CH:15][CH:16]=2)=[O:28])[CH:41]=1)([CH3:45])([CH3:43])[CH3:44]

Komponenten

7

Edukt 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 10214710N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamideHCID 59379818[4-(2-Morpholin-4-yl-pyrimidin-4-yl-oxy)-naphthalen-1-yl]-oxo-acetic acid

Produkt 1

HCID 16734161N-(5-tert-butyl-2-methoxy-3-(methylsulfonamido)phenyl)-2-(4-(2-morpholinopyrimidin-4-yloxy)naphthalen-1-yl)-2-oxoacetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

[4-(2-Morpholin-4-yl-pyrimidin-4-yl-oxy)-naphthalen-1-yl]-oxo-acetic acid (16) obtained above (36 mg, 0.095 mmol) was dissolved in 2 mL DCM and oxalyl chloride (0.08 mL, 0.949 mmol) was added, followed by catalytic DMF. The reaction mixture was stirred at rt, after which N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide (14) (26 mg, 0.096 mmol) and DIEA (0.05 mL, 0.284 mmol) were added, and stirring was continued for 12 hr. The reaction mixture was concentrated in vacuo and the residue was purified by LC/MS (10-100% AcN/H2O over 8.5 min.) Calculated mass=444. Observed mass=444.

Aufarbeitung

  1. stirringstirring
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by LC/MS (10-100% AcN/H2O over 8.5 min.)

Quellen und Nachweise

ORD-Eintrag
ord-fd08995cf32043a2b4ac89b48fd0b29d
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07749999B2

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