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Diethyl Ether → [4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid

HRID 241040
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 241040
Cl.[O:2]1[C:8]2[CH:9]=[CH:10][C:11]([B:13]([OH:15])[OH:14])=[CH:12][C:7]=2[CH2:6][NH:5][CH2:4][CH2:3]1.Cl[C:17]1[C:26]2[CH2:25][C:24]([CH3:28])([CH3:27])[CH2:23][CH2:22][C:21]=2[N:20]=[CH:19][N:18]=1.CCN(C(C)C)C(C)C.C(OCC)C>O1CCOCC1.O>[CH3:27][C:24]1([CH3:28])[CH2:23][CH2:22][C:21]2[N:20]=[CH:19][N:18]=[C:17]([N:5]3[CH2:6][C:7]4[CH:12]=[C:11]([B:13]([OH:15])[OH:14])[CH:10]=[CH:9][C:8]=4[O:2][CH2:3][CH2:4]3)[C:26]=2[CH2:25]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 66820605(2,3,4,5-Tetrahydrobenzo[f][1,4]oxazepin-7-yl)boronic acid hydrochlorideHCID 866478114-Chloro-6,6-dimethyl-5,6,7,8-tetrahydroquinazoline

Produkt 1

HCID 66820411[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid
Ausbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a slurry of 2,3,4,5-tetrahydro-1,4-benzoxazepin-7-ylboronic acid hydrochloride salt (5.7 g, 25 mmol) (example 8, step 1) and 4-chloro-6,6-dimethyl-5,6,7,8-tetrahydroquinazoline (reagent preparation 3) (3.0 g, 15 mmol) in dioxane (75 mL) and H2O (75 mL) was added DIPEA (17 mL, 100 mmol) and the resulting mixture was heated (90° C.). After 72 hours the solution was concentrated and partitioned between 2M aqueous sodium hydroxide and ethyl ether. The aqueous layer was neutralized and extracted with chloroform. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Trituration with ethyl ether provided [4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid (4.2 g, 80% yield) as a white solid. 1H NMR (400 MHz, d6-DMSO) δ 8.68 (s, 1H), 7.77 (s, 1H), 7.64 (dd, 1H), 6.86 (dd, 1H), 5.04 (s, 2H), 4.46 (m, 2H), 4.18 (m, 2H), 2.80 (t, 2H), 2.52 (s, 2H), 1.58 (t, 2H), 0.86 (s, 6H); MS (ES) for C19H24BN3O3: 354 (MH+).

Aufarbeitung

  1. concentrationAfter 72 hours the solution was concentrated
  2. custompartitioned between 2M aqueous sodium hydroxide and ethyl ether
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f00c26ca92ac417e8ef6eeca02513cbc
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08648066B2

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