Diisopropylethylamine → HCID 178493823, Verbindung

HRID 536245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 536245
[CH3:1][O:2][C:3]1[C:12]2[N:11]=[C:10]([NH2:13])[N:9]3[CH2:14][CH2:15][N:16]=[C:8]3[C:7]=2[CH:6]=[CH:5][C:4]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1.[NH2:29][C:30]1[N:35]=[CH:34][C:33]([C:36](O)=[O:37])=[CH:32][N:31]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[NH2:29][C:30]1[N:35]=[CH:34][C:33]([C:36]([NH:13][C:10]2[N:9]3[CH2:14][CH2:15][N:16]=[C:8]3[C:7]3[CH:6]=[CH:5][C:4]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=4)=[C:3]([O:2][CH3:1])[C:12]=3[N:11]=2)=[O:37])=[CH:32][N:31]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 70203672-aminopyrimidine-5-carboxylic AcidHCID 178493824HCID 178493824, Verbindung

Produkt 1

HCID 178493823HCID 178493823, VerbindungAusbeute 12,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

7-Methoxy-8-{[4-(methylsulfonyl)benzyl]oxy}-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine (Step 1, 76 mg, 0.19 mmol) was dissolved in DMF (5 mL), and 2-aminopyrimidine-5-carboxylic acid (40 mg, 0.29 mmol) was added. PyBOP (152 mg, 0.29 mmol) and diisopropylethylamine (0.15 mL, 0.85 mmol) were subsequently added. The mixture was stirred at it overnight, during which a tan solid precipitated. The DMF was removed under reduced pressure and the residue purified via silica gel chromatography (0-3% MeOH/CH2Cl2+0.1% Et3N). The solvent was evaporated under reduced pressure, the residue triturated in water (5 mL), collected by vacuum filtration, then washed with acetone. High vacuum drying gave the title compound (12 mg, 12%): HPLC MS RT=2.06 min, MH+=522.1; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 3.22 (3H, s), 4.00 (3H, s), 4.19-4.25 (2H, m), 4.48-4.55 (2H, m), 5.53 (2H, s), 7.53 (1H, d), 7.77 (2H, d), 7.97-8.03 (3H, m), 9.06 (2H, s).

Aufarbeitung

  1. customprecipitated
  2. customThe DMF was removed under reduced pressure
  3. customthe residue purified via silica gel chromatography (0-3% MeOH/CH2Cl2+0.1% Et3N)
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue triturated in water (5 mL)
  6. filtrationcollected by vacuum filtration
  7. washwashed with acetone
  8. customHigh vacuum drying

Quellen und Nachweise

ORD-Eintrag
ord-4511cf258c8f412eb912933c7e37f00a
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859572B2

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