Acrylic Acid → HCID 10523147, Verbindung

HRID 394754

Reaktionsgleichung

Reaktionsgleichung von HRID 394754
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)[C:10]=2[N:11]=1.[C:20](O)(=[O:23])[CH:21]=[CH2:22].Cl.CN(C)CCCN=C=NCC.CCOC(C)=O.C(Cl)Cl>CC(N(C)C)=O.C(Cl)Cl.CCCCCC.CO.C(Cl)Cl.CCOC(C)=O>[Br:19][C:15]1[CH:14]=[C:13]([NH:12][C:9]2[C:10]3[N:11]=[C:2]([NH:1][C:20](=[O:23])[CH:21]=[CH2:22])[CH:3]=[CH:4][C:5]=3[N:6]=[CH:7][N:8]=2)[CH:18]=[CH:17][CH:16]=1

Komponenten

8

Edukt 4

HCID 6581Acrylic Acid2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 53282744-N-(3-bromophenyl)pyrido[3,2-d]pyrimidine-4,6-diamineHCID 21226138Dichloromethane ethylacetate

Produkt 1

HCID 10523147HCID 10523147, VerbindungAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 31374DimethylacetamideLösungsmittelHCID 21226440Methylenechloride HexaneLösungsmittelHCID 21901258Dichloromethane ethyl acetate methanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 6-amino-4-[(3-bromo-phenyl)amino]pyrido[3,2-d]pyrimidine (J Med Chem, 1996;39:1823) (46 mg, 0.15 mmol) and acrylic acid (6 mol eq., 0.91 mmol, 62 μL) in DMA (5.0 mL) under N2 was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI.HCl) (4.0 mol eq., 0.61 mmol, 116 mg). The reaction mixture was stirred for 48 hours with additional amounts of acrylic acid and EDCI.HCl (62 μL/116 mg) being added every 12 hours it was then worked up as above to give after chromatography on silica gel eluting with EtOAc:CH2Cl2 (1:1) to MeOH/CH2Cl2/EtOAc (2:48:50), N-[4-[(3-bromophenyl)-amino]pyrido[3,2 -d]pyrimidin-6-yl]acrylamide (14 mg, 26%) as a cream powder, mp (CH2Cl2/hexane) 226-228° C.

Aufarbeitung

  1. additionbeing added every 12 hours it

Quellen und Nachweise

ORD-Eintrag
ord-74e3ef88c60b4122bd3f1a50ca0f92b0
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06602863B1

Verknüpfte Notizen

Wird geladen…