HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Diisopropylethylamine → 3-{1-[(3-chloro-4-fluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| Edukt | 2-(3-Chloro-4-fluorophenyl)acetic acid | HCID 2773721 | — |
| Edukt | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Edukt | 3(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 2HCl | HCID 66823550 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | 3-{1-[(3-chloro-4-fluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine | HCID 66823736 | — |
Reaktionsschritte
In a 20 mL vial with cap, to the solution of 3-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 2HCl (64.6 mg, 0.190 mmol), (3-chloro-4-fluorophenyl)acetic acid (35.9 mg, 0.190 mmol), HATU (72.4 mg, 0.190 mmol) in DMF (2 mL) was added Hunig's base (0.133 mL, 0.762 mmol). The mixture was stirred overnight. The reaction was poured into water, and an off-white solid formed. The solid was filtered to give the title compound as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.22-3.30 (m, 2H), 3.94 (s, 5H), 4.26 (t, J=8.46 Hz, 2H), 7.33 (dd, J=4.93, 2.15 Hz, 1H), 7.37-7.40 (m, 1H), 7.41-7.47 (m, 1H), 7.51-7.58 (m, 2H), 8.18 (d, J=8.59 Hz, 1H), 8.25 (s, 1H).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08598156B2 |
| Quelldatensatz | uspto-grants-2013_12 |
| ORD ID | ord-d267c8a44ff14b5ea3ca5e19f10d2d25 |
| Quellennotiz | uspto-grants-2013_12 |