Sodium Hydroxide → Doxazosin

HRID 428360

반응식

HRID 428360 반응식
[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]

참가 물질

3

반응물 2

HCID 14798Sodium HydroxideHCID 11591230Doxazosin Monohydrochloride

생성물 1

HCID 3157Doxazosin

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-69da2c6d5cec485f9abdf4cf929fe71a
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313293B1

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