(4R)-4-[(4-amino-1-piperidinyl)methyl]-3-fluoro-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one → Isopropylamine

Participants

Role	Name	HCID	Charge
Reactant	(4R)-4-[(4-amino-1-piperidinyl)methyl]-3-fluoro-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one	HCID 23633344	—
Reactant	(4S)-4-[(4-amino-1-piperidinyl)methyl]-3,8-difluoro-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one	HCID 23633410	—
Product	Isopropylamine	HCID 6363	—
Product	(4R)-4-[(4-amino-1-piperidinyl)methyl]-3-fluoro-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one	HCID 23633344	—
Product	(4S)-4-[(4-amino-1-piperidinyl)methyl]-3,8-difluoro-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one	HCID 23633410	—

Reaction Steps

(4R/S)-4-({4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]-1-piperidinyl}methyl)-3,4-difluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-1-one (43 mg) was resolved by preparative chiral HPLC into the two enantiomers E1 and E2 using a Chiralpak AD-H column, eluting with 50:50:0.1 acetonitrile:methanol:isopropylamine, affording enantiomers E1 (first eluting) and E2 (second eluting) which were converted to the mono hydrochloride salts by dissolving in methanol, adding 1 equivalent of aqueous 6.0N HCl and evaporating to dryness.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07732460B2
Source dataset	uspto-grants-2010_06
ORD ID	ord-4082a28ab5ba4005a212004508e091d1
Source note	uspto-grants-2010_06