Methanimidamide, hydrochloride (1:1) → 7-(3-chloropropoxy)-6-methoxy-1H-quinazolin-4-one

HRID 631256Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 631256
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][CH2:14][CH2:15][Cl:16])=[CH:6][C:5]=1[NH2:17].Cl.[CH:20](N)=[NH:21]>C(O)C>[Cl:16][CH2:15][CH2:14][CH2:13][O:12][C:7]1[CH:6]=[C:5]2[C:4]([C:3]([OH:2])=[N:21][CH:20]=[N:17]2)=[CH:9][C:8]=1[O:10][CH3:11]

Komponenten

4

Edukt 2

HCID 10313058Methanimidamide, hydrochloride (1:1)HCID 23033013Methyl 2-amino-4-(3-chloropropoxy)-5-methoxybenzoate

Produkt 1

HCID 1784867697-(3-chloropropoxy)-6-methoxy-1H-quinazolin-4-oneAusbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of the intermediate from Step 3 (4.2 g, 15.35 mmol) in ethanol was added formamidine hydrochloride (2.97 g, 36.96 mmol). The mixture was heated at 140° C. in sealed tube for 12h. Completion of the reaction was monitored by LCMS. The precipitate formed was filtered and washed with ethanol and dried to afford the pure compound 7-(3-chloro-propoxy)-6-methoxy-quinazolin-4-ol (2.32 g, 56%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 11.93 (brs, 1H), 7.99 (s, 1H), 7.45 (s, 1H), 7.16 (s, 1H), 4.23 (t, 2H), 3.88 (s, 3H), 3.80 (t, 2H), 2.23 (t, 2H), LC-MS (ESI)m/z 269 (M+H)+.

Aufarbeitung

  1. customThe precipitate formed
  2. filtrationwas filtered
  3. washwashed with ethanol
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-37bd88eb542544758bc931cd117bc5fd
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09320739B2

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