Sodium Hydroxide → Doxazosin

HRID 428360

反応式

HRID 428360 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:9]([NH2:31])=[N:10][C:11]([N:13]3[CH2:18][CH2:17][N:16]([C:19]([CH:21]4[O:30][C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[O:23][CH2:22]4)=[O:20])[CH2:15][CH2:14]3)=[N:12][C:6]2=[CH:5][C:4]=1[O:32][CH3:33].Cl.[OH-].[Na+]>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:9]([NH2:31])=[N:10][C:11]([N:13]3[CH2:14][CH2:15][N:16]([C:19]([CH:21]4[O:30][C:29]5[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=5[O:23][CH2:22]4)=[O:20])[CH2:17][CH2:18]3)=[N:12][C:6]2=[CH:5][C:4]=1[O:32][CH3:33]

参加物

3

反応物 2

HCID 14798Sodium HydroxideHCID 11591230Doxazosin Monohydrochloride

生成物 1

HCID 3157Doxazosin

実験手順

4-Amino-2-chloro-6,7-bismethoxyquinazoline (III) (3.2 grams, 13.35 mmole), Compound 4 from Example 2 (3.4 grains, 13.75 mmole) and n-butanol (72 ml) were subjected to a 50 ml round-bottom flask and heated under refluxing for 3.5 hours under a nitrogen atmosphere. Cooling to 75° C., the solid products were filtered and collected, dried in an oven to obtain 5.25 grams of Doxazosin hydrochloride (10.76 mmole, Yield: 81%). The Doxazosin hydrochloride was added to a 1N NaOH solution and heated for dissolution. After cooling, the solution was extracted with 150 ml of dichloromethane twice. The organic layer was filtered and dried with anhydrous sulfate, and concentrated to obtain 4.61 grams of white Doxazosin solid: 1H NMR (CDCl3) δ 3.63-4.09 (m, 8 H), 3.91 (s, 3H), 3.96 (s, 3H), 4.35 (dd, J=11.9, 7.9 Hz, 1H), 4.52 (dd, J=11.9, 2.4 Hz, 1H), 4.88 (dd, J=7.9, 2.4 Hz, 1H), 6.85-6.95 (m, 5H)

後処理

  1. temperatureheated for dissolution
  2. temperatureAfter cooling
  3. extractionthe solution was extracted with 150 ml of dichloromethane twice
  4. filtrationThe organic layer was filtered
  5. dry with materialdried with anhydrous sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-69da2c6d5cec485f9abdf4cf929fe71a
出典データセット
uspto-grants-2001_11
特許番号
US06313293B1

関連ノート

読み込み中…