1-[4-(2-(Azepan-1-yl)ethoxy)benzyl]-5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indole → Bazedoxifene

HRID 1862562노트

반응식

HRID 1862562 반응식
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:21][CH:20]=1)[C:13]([C:35]1[CH:40]=[CH:39][C:38]([O:41]CC3C=CC=CC=3)=[CH:37][CH:36]=1)=[C:12]2[CH3:49])C1C=CC=CC=1>C1COCC1.CCO>[N:28]1([CH2:27][CH2:26][O:25][C:22]2[CH:21]=[CH:20][C:19]([CH2:18][N:14]3[C:15]4[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=4)[C:12]([CH3:49])=[C:13]3[C:35]3[CH:36]=[CH:37][C:38]([OH:41])=[CH:39][CH:40]=3)=[CH:24][CH:23]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

참가 물질

3

반응물 1

HCID 98958311-[4-(2-(Azepan-1-yl)ethoxy)benzyl]-5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indole

생성물 1

HCID 154257Bazedoxifene

시약·촉매·용매 1

HCID 21873804Tetrahydrofuran ethanol용매

실험 절차

A solution consisting of indole 44 (17.5g, 26.9 mmol) in THF/EtOH (1:1) was hydrogenated under an atmosphere of H2 using 10% Pd/C as a catalyst. Chromatography on silica gel CH2Cl2/MeOH (gradient from 100/0 to 85/15) yields the desired product as 8.5 g of white foam along with 2.5 g of a fraction containing small impurities. Although the free base is the material used in the next step (bis-glucuronidation), for purposes of characterization and enhancing the compounds shelf life an acid addition salt may be made with HCl by dissolving the compound in MeOH and treating with 1.1 eq of a 2 N aq HCl solution. The compound slowly precipitates out as white crystals. Physical data listed below describes the HCl salt of indole 45:

출처 및 근거

ORD 기록
ord-fa4dfd38c6944c3ca10afd6a3617661b
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06537971B2

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