Triethylamine → HCID 178476959, Verbindung

HRID 1525333Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1525333
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:11][C:12]([C:14]2[C:15]([OH:26])=[N:16][C:17]([C:20]3[N:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[N:18][CH:19]=2)=[O:13])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH2:27]([O:29][P:30]([O-:34])[O:31][CH2:32][CH3:33])[CH3:28].CCN(CC)CC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:26][C:15]1[C:14]([C:12]([NH:11][C:8]([C:5]2[CH:6]=[CH:7][C:2]([P:30](=[O:34])([O:31][CH2:32][CH3:33])[O:29][CH2:27][CH3:28])=[CH:3][CH:4]=2)([CH3:10])[CH3:9])=[O:13])=[CH:19][N:18]=[C:17]([C:20]2[N:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[N:16]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 3780918DiethylphosphiteHCID 178457728HCID 178457728, Verbindung

Produkt 1

HCID 178476959HCID 178476959, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of N-(2-(4-bromophenyl)propan-2-yl)-4-hydroxy-2-(pyridazin-3-yl)pyrimidine-5-carboxamide (36-c, 200 mg, 0.484 mmol), diethylphosphite (195 mg, 1.45 mmol), Et3N (146 mg, 1.45 mmol) and Pd (PPh3)4 (0.1 g) in toluene (10 mL) was refluxed overnight. The reaction mixture was concentrated in vacuum. The residue was purified by pre-HPLC to afford the product 36-d, (3.0 mg). 1H NMR (300 MHz, DMSO) δ10.85 (s, 1H), 9.08 (s, 1H), 8.75 (d, J=8.4 Hz), 7.86 (m, 1H), 7.61-7.52 (m, 2H), 7.43-7.42 (m, 2H), 4.00-3.92 (m, 4H), 1.61 (s, 6H), 1.20 (t, J=6.9 Hz, 6H). LC-MS: (M+H)+ 472.

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. concentrationThe reaction mixture was concentrated in vacuum
  3. customThe residue was purified by pre-HPLC
  4. customto afford the product 36-d, (3.0 mg)

Quellen und Nachweise

ORD-Eintrag
ord-ad98f37461ef4dd19603384ba39b9730
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079930B2

Notizen zur Reaktion

Wird geladen…