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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
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HRID 241040 반응식
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
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참가 물질

7

반응물 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

생성물 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 acid수율 80%

시약·촉매·용매

2
HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-f00c26ca92ac417e8ef6eeca02513cbc
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08648066B2

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