Trifluoroacetic acid → HCID 178493872, Verbindung

HRID 536256Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 536256
C(OC(=O)[NH:7][C:8]1[N:13]=[CH:12][C:11]([C:14](=[O:44])[NH:15][C:16]2[N:25]3[CH2:26][CH2:27][N:28]=[C:24]3[C:23]3[CH:22]=[CH:21][C:20]([O:29][CH2:30][CH2:31][CH2:32][S:33]([N:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)(=[O:35])=[O:34])=[C:19]([O:42][CH3:43])[C:18]=3[N:17]=2)=[CH:10][N:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.CCN(CC)CC>[NH2:7][C:8]1[N:13]=[CH:12][C:11]([C:14]([NH:15][C:16]2[N:25]3[CH2:26][CH2:27][N:28]=[C:24]3[C:23]3[CH:22]=[CH:21][C:20]([O:29][CH2:30][CH2:31][CH2:32][S:33]([N:36]4[CH2:37][CH2:38][O:39][CH2:40][CH2:41]4)(=[O:35])=[O:34])=[C:19]([O:42][CH3:43])[C:18]=3[N:17]=2)=[O:44])=[CH:10][N:9]=1

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 178493871HCID 178493871, Verbindung

Produkt 1

HCID 178493872HCID 178493872, VerbindungAusbeute 121,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8471TriethylamineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

tert-Butyl[5-({7-methoxy-8-[3-(morpholin-4-ylsulfonyl)propoxy]-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl}carbamoyl)pyrimidin-2-yl]carbamate (Step 1, 150 mg 0.26 mmol) was dissolved in CH2Cl2 (15 mL) and TFA (0.16 mL, 2.1 mmol) was added dropwise. The mixture was stirred at rt over 2 d, after which 5 drops of Et3N were added causing a solid to precipitate. The mixture was stirred overnight, then the solvents removed under reduced pressure. The resulting residue was triturated in EtOAc (15 mL), collected by vacuum filtration and washed further with EtOAc (10 mL). This solid was then triturated in water (5 mL) collected by vacuum filtration and washed further with water (10 mL). High vacuum drying gave the title compound (172 mg, 92%): HPLC MS RT=0.87 min, MH+=545.2; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 2.21-2.26 (2H, m), 3.15-3.18 (4H, m), 3.24-3.29 (2H, m), 3.61-3.65 (4H, m), 3.99 (3H, s), 4.18-4.25 (2H, m), 4.37 (2H, t), 4.48-4.55 (2H, m), 7.44 (1H, d), 8.02 (1H, d), 9.06 (2H, s).

Aufarbeitung

  1. customto precipitate
  2. stirringThe mixture was stirred overnight
  3. customthe solvents removed under reduced pressure
  4. customThe resulting residue was triturated in EtOAc (15 mL)
  5. filtrationcollected by vacuum filtration
  6. washwashed further with EtOAc (10 mL)
  7. customThis solid was then triturated in water (5 mL)
  8. filtrationcollected by vacuum filtration
  9. washwashed further with water (10 mL)
  10. customHigh vacuum drying

Quellen und Nachweise

ORD-Eintrag
ord-478d0b13b275412a8c83c105a3c4e0e9
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859572B2

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