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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1051375Generated: October 27, 2026

L-Alaninol → 3-((3S,4S)-3-Fluoro-tetrahydro-pyran-4-ylamino)-isoquinoline-6-carboxylic acid [(S)-2-hydroxy-1-(4-methoxy-phenyl)-ethyl]-amide

https://huagongshe.com/reaction/1051375

Reaction equation

Participants

RoleNameHCIDCharge
ReactantL-AlaninolHCID 80307—
ReactantHCID 68295107HCID 68295107—
Reactant(S)-2-Amino-2-(4-methoxyphenyl)ethanol hydrochlorideHCID 70141372—
Reactant(S)-(3-fluoro-4-methoxy-phenyl)-(1-methylpyrazol-4-yl)methanamine hydrochlorideHCID 86712001—
Product3-((3S,4S)-3-Fluoro-tetrahydro-pyran-4-ylamino)-isoquinoline-6-carboxylic acid [(S)-2-hydroxy-1-(4-methoxy-phenyl)-ethyl]-amideHCID 73336137—

Reaction Steps

3-((3S,4S)-3-Fluoro-tetrahydro-pyran-4-ylamino)-isoquinoline-6-carboxylic acid [(S)-2-hydroxy-1-(4-methoxy-phenyl)-ethyl]-amide (II-43) was prepared analogously except in step 2, (S)-2-aminopropan-1-ol was replaced with (3S,4S)-3-fluorotetrahydro-2H-pyran-4-amine (71c) and in step 5, 50c was replaced with (S)-2-amino-2-(4-methoxyphenyl)ethanol hydrochloride (62c). 1H NMR (500 MHz, DMSO-d6): δ 8.93 (s, 1H), 8.80 (d, J=8.5 Hz, 1H), 8.09 (s, 1H), 7.87 (d, J=9.0 Hz, 1H), 7.56 (d, J=9.0 Hz, 1H), 7.33 (d, J=8.5 Hz, 2H), 6.90 (s, 1H), 6.89 (d, J=8.5 Hz, 2H), 6.67 (d, J=8.5 Hz, 1H), 5.07-5.02 (m, 1H), 4.92 (t, J=11.5 Hz, 1H), 4.78 (d, J=50.0 Hz, 1H), 4.30-4.20 (m, 1H), 4.05-3.99 (m, 1H), 3.94-3.90 (m, 1H), 3.73-3.50 (m, 7H), 1.92-1.80 (m, 1H), 1.75-1.70 (m, 1H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09388171B2
Source datasetuspto-grants-2016_07
ORD IDord-c82a85895ddb4c52b3a4558b63f82d0b
Source noteuspto-grants-2016_07