L-Alaninol → N-((S)-2-Hydroxy-1-(4-methoxyphenyl)ethyl)-3-(tetrahydrofuran-3-ylamino)isoquinoline-6-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	L-Alaninol	HCID 80307	—
Reactant	Oxolan-3-amine	HCID 3365553	—
Reactant	(S)-2-Amino-2-(4-methoxyphenyl)ethanol hydrochloride	HCID 70141372	—
Reactant	(S)-(3-fluoro-4-methoxy-phenyl)-(1-methylpyrazol-4-yl)methanamine hydrochloride	HCID 86712001	—
Product	N-((S)-2-Hydroxy-1-(4-methoxyphenyl)ethyl)-3-(tetrahydrofuran-3-ylamino)isoquinoline-6-carboxamide	HCID 73335754	—

Reaction Steps

N—((S)-2-Hydroxy-1-(4-methoxyphenyl)ethyl)-3-(tetrahydrofuran-3-ylamino)isoquinoline-6-carboxamide (II-21) was prepared analogously except in step 2, (S)-2-aminopropan-1-ol was replaced with 3-amino-tetrahydrofuran and in step 5, 50c was replaced with 62c. 1H NMR (500 MHz, DMSO-d6) δ 8.93 (s, 1H), 8.78 (d, J=8 Hz, 1H), 8.10 (s, 1H), 7.86 (d, J=8.5 Hz, 1H), 7.55 (dd, J=8.5, 1.5 Hz, 1H), 7.33 (d, J=9.0 Hz, 2H), 6.89 (d, J=9.0 Hz, 2H), 6.82 (d, J=6.0 Hz, 1H), 6.70 (s, 1H), 5.04 (m, 1H), 4.91 (t, J=6.0 Hz, 1H), 4.30 (m, 1H), 3.95 (m, 1H), 3.86 (m, 1H), 3.77-3.64 (m, 5H), 3.62-3.60 (m, 2H), 2.23 (m, 1H), 1.87 (m, 1H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09388171B2
Source dataset	uspto-grants-2016_07
ORD ID	ord-da120f262e7d4c4e8ef30b3605349b6e
Source note	uspto-grants-2016_07