HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-(4-Iodo-3-methoxy-pyrazol-1-yl)-propan-1-ol → 3-amino-6-[1-(3-hydroxypropyl)-3-methoxy-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-(4-Iodo-3-methoxy-pyrazol-1-yl)-propan-1-ol | HCID 67814064 | — |
| Reactant | 3-amino-N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide | HCID 67818926 | — |
| Reactant | 2-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide | HCID 86697680 | — |
| Product | 3-amino-6-[1-(3-hydroxypropyl)-3-methoxy-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide | HCID 86697780 | 30% |
Reaction Steps
Prepared analogously to Compound 3C using 3-amino-N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide (Compound 48D, 500 mg, 2 mmol) and 3-(4-iodo-3-methoxy-pyrazol-1-yl)-propan-1-ol (Compound 48E, 600 mg, 2.18 mmol) to afford 177 mg of the title compound (30%). 1H NMR (400 MHz, CD3OD) δ 8.13 (s, 1H), 7.67 (d, J=8.8 Hz, 1H), 7.11 (d, J=8.8 Hz, 1H), 4.11 (t, J=6.8 Hz, 2H), 3.98 (s, 3H), 3.57 (t, J=6.2 Hz, 2H), 2.93 (s, 3H), 2.05 (t, J=6.4 Hz, 2H). MS (ESI): m/z=306.24 [M+H]+. UPLC: tR=0.75 min (UPLC-TOF: polar—2 min).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09133224B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-01a4d5d294ed44e9963beaf36897668d |
| Source note | uspto-grants-2015_09 |