3-(2-Cyanoethylaminocarbonyl)benzeneboronic acid → 3-(2'-amino-1'-methyl-5'-oxo-2-phenyl-1',5'-dihydrospiro[chroman-4,4'-imidazole]-6-yl)-N-(2-cyanoethyl)benzamide

HRID 1408644

Reaktionsgleichung

Reaktionsgleichung von HRID 1408644
[NH2:1][C:2]1[N:3]([CH3:24])[C:4](=[O:23])[C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=3)[O:9][CH:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:7]2)[N:6]=1.[C:25]([CH2:27][CH2:28][NH:29][C:30]([C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1)=[O:31])#[N:26]>O1CCOCC1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[N:3]([CH3:24])[C:4](=[O:23])[C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:36]4[CH:37]=[C:32]([CH:33]=[CH:34][CH:35]=4)[C:30]([NH:29][CH2:28][CH2:27][C:25]#[N:26])=[O:31])[CH:14]=3)[O:9][CH:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:7]2)[N:6]=1

Komponenten

6

Edukt 2

HCID 36905983-(2-Cyanoethylaminocarbonyl)benzeneboronic acidHCID 584237682'-amino-6-bromo-1'-methyl-2-phenylspiro[chroman-4,4'-imidazol]-5'(1'H)-one

Produkt 1

HCID 673850213-(2'-amino-1'-methyl-5'-oxo-2-phenyl-1',5'-dihydrospiro[chroman-4,4'-imidazole]-6-yl)-N-(2-cyanoethyl)benzamideAusbeute 8,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 10796Cesium carbonateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Pd(PPh3)2Cl2 (10 mg) in a 10 mL CEM test tube under Ar was treated sequentially with 2′-amino-6-bromo-1′-methyl-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (20 mg, 0.05 mmol) in 1,4-dioxane (1 mL), Cs2CO3 (2 N, 0.3 mL) and 3-(2-cyanoethyl-carbamoyl)phenylboronic acid (22 mg, 0.1 mmol). The mixture was heated in a microwave reactor at 120° C. for 30 mins. The reaction mixture was concentrated in vacuo to give the residue, which was purified by preparative TLC to give pure 3-(2′-amino-1′-methyl-5′-oxo-2-phenyl-1′,5′-dihydrospiro[chroman-4,4′-imidazole]-6-yl)-N-(2-cyanoethyl)benzamide (1.96 mg, 8%). 1H-NMR (MeOD): 2.52 (m, 1H), 2.64 (m, 1H), 2.83 (t, 2H), 3.35 (s, 3H), 3.68 (t, 2H), 5.86 (d, 1H), 7.18 (d, 1H), 7.43 (m, 3H), 7.55 (m, 3H), 7.57 (d, 1H), 7.71 (d, 1H), 7.79 (m, 2H), 8.05 (s, 1H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give the residue, which
  3. customwas purified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-52857edcb06c41099de6dbfd4aec87d6
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921359B2

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