HuagongsheHuagongshe Chemistry Print Report · For research reference only
L-Alaninol → 3-(Tetrahydro-pyran-4-ylamino)-isoquinoline-6-carboxylic acid [(S)-1-(3-fluoro-4-methoxy-phenyl)-2-hydroxy-ethyl]-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | L-Alaninol | HCID 80307 | — |
| Reactant | 4-Aminotetrahydropyran | HCID 419223 | — |
| Reactant | (S)-(3-fluoro-4-methoxy-phenyl)-(1-methylpyrazol-4-yl)methanamine hydrochloride | HCID 86712001 | — |
| Reactant | (S)-2-Amino-2-(3-fluoro-4-methoxyphenyl)ethanol hydrochloride | HCID 86712007 | — |
| Product | 3-(Tetrahydro-pyran-4-ylamino)-isoquinoline-6-carboxylic acid [(S)-1-(3-fluoro-4-methoxy-phenyl)-2-hydroxy-ethyl]-amide | HCID 73335358 | — |
Reaction Steps
3-(Tetrahydro-pyran-4-ylamino)-isoquinoline-6-carboxylic acid [(S)-1-(3-fluoro-4-methoxy-phenyl)-2-hydroxy-ethyl]-amide (II-17) was prepared analogously except in step 2, (S)-2-aminopropan-1-ol was replaced with 4-amino-tetrahydropyran and in step 5, 50c was replaced with (S)-2-amino-2-(3-fluoro-4-methoxyphenyl)ethanol hydrochloride (62d). 1H NMR (500 MHz, DMSO-d6) δ 8.91 (s, 1H), 8.76 (d, J=8.5 Hz, 1H), 8.08 (s, 1H), 7.85 (d, J=8.5 Hz, 1H), 7.53 (d, J=9.0 Hz, 1H), 7.27 (d, J=13.0 Hz, 1H), 7.17 (d, J=8.5 Hz, 1H), 7.11 (t, J=8.5 Hz, 1H), 6.73 (s, 1H), 6.55 (d, J=8.0 Hz, 1H), 5.06-5.02 (m, 1H), 4.96 (t, J=5.5 Hz, 1H), 3.91-3.89 (m, 2H), 3.81 (s, 3H), 3.70-3.61 (m, 2H), 3.46-3.42 (m, 3H), 1.94-1.91 (m, 2H), 1.52-1.45 (m, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09388171B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-8d64b0ecc86e45fbabc45d9f3428ac68 |
| Source note | uspto-grants-2016_07 |