N-[(1S,5R)-7,9-dimethyl-7,9-diazabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide dihydrochloride

N-[(1S,5R)-7,9-dimethyl-7,9-diazabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide dihydrochloride 구조식 이미지
카스 번호:
160472-97-9
상품명:
N-[(1S,5R)-7,9-dimethyl-7,9-diazabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide dihydrochloride
동의어(영문):
N3389T;N 3389T;N-3389T;Sinseron;Indisetron hydrochloride;Indisetron Dihydrochloride;N-[(1S,5R)-3,9-dimethyl-3,9-diazabicyclo[3.3.1]nonan-7-yl]-1H-indazole-3-carboxamide;N-[(1S,5R)-7,9-dimethyl-7,9-diazabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide dihydrochloride;N-[(1S,5R)-3,9-DIMETHYL-3,9-DIAZABICYCLO[3.3.1]NONAN-7-YL]-1H-INDAZOLE-3-CARBOXAMIDE;DIHYDROCHLORIDE
CBNumber:
CB61459566
분자식:
C17H24ClN5O
포뮬러 무게:
349.86
MOL 파일:
160472-97-9.mol

N-[(1S,5R)-7,9-dimethyl-7,9-diazabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide dihydrochloride 속성

안전

N-[(1S,5R)-7,9-dimethyl-7,9-diazabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide dihydrochloride C화학적 특성, 용도, 생산

Originator

Nisshin (Japan)

상표명

Sinseron

Synthesis

The synthesis is highlighted in the Scheme. Bromoacetaldehyde dimethyl acetal (44) was condensed with methylamine with KOH in refluxing ethyleneglycol for 3 hr to give 33% yield of bis(2,2-dimethoxyethyl)amine (45), which was cyclized with acetonedicarboxylic acid (46) and methylamine to generate 3,9-dimethyl-3,9-diazabicyclo- [3.3.1]nonan-7-one (47) in 12% yield. Compound 47 was reacted with hydroxylamine in refluxing pyridine and ethanol mixture to give corresponding oxime 48 in 88% yield, which was subsequently reduced with hydrogen over Raney Ni in hot ethanol in the presence of ammonium acetate at 50 kg/cm2 to give amine 49 in 89% yield. Compound 49 was condensed with 1H-indazole-3-carbonyl chloride (50) in pyridine with catalytic amount of DMAP to give crude indisteron free base, which was re-crystallized from chloroform/hexane to give indisteron free base as colorless crystals in 16% yield. Finally, the free base was treated with hydrogen chloride to give indisteron hydrochloride (VII).

Synthesis_160472-97-9

N-[(1S,5R)-7,9-dimethyl-7,9-diazabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide dihydrochloride 준비 용품 및 원자재

원자재

준비 용품


N-[(1S,5R)-7,9-dimethyl-7,9-diazabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide dihydrochloride 공급 업체

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