Chloroform → 3-Fluoro-4-({(3R,4S)-4-[(3,4-dihydro-2H-pyrano[2,3-c]pyridin-6-ylmethyl)amino]-3-hydroxy-1-piperidinyl}methyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Hydrochloride

참여 물질

역할	이름	HCID	투입량
반응물	Chloroform	HCID 6212	—
반응물	Sodium triacetoxyborohydride	HCID 5049666	—
반응물	3,4-dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehyde	HCID 56640311	—
반응물	trans-4-(Boc-amino)-3-hydroxypiperidine	HCID 57525698	—
반응물	4-{[(3R,4S)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one	HCID 68686175	—
용매	Methanol	HCID 887	—
생성물	3-Fluoro-4-({(3R,4S)-4-[(3,4-dihydro-2H-pyrano[2,3-c]pyridin-6-ylmethyl)amino]-3-hydroxy-1-piperidinyl}methyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Hydrochloride	HCID 68686877	70%

반응 단계

A mixture of 4-{[(3R,4S)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Diastereomer 1 (54 mg), 3,4-dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehyde (for a synthesis see WO2004058144, Example 126(c)) (20.6 mg) and 3A molecular sieves in chloroform (1 ml) and methanol (1 ml) was heated at 65° C. for 5 h, cooled and then sodium triacetoxyborohydride (53 mg) was added. The general procedure of Example 72 was then followed to obtain the free base of the title compound (41 mg, 70%).

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US07732461B2
출처 데이터셋	uspto-grants-2010_06
ORD ID	ord-5c694ce8a0b14c81a0674c18c4f5849b
출처 메모	uspto-grants-2010_06