HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Tert-butyl (6-carbamoyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | Tert-butyl (6-carbamoyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate | HCID 57691087 | — |
| Reactant | 3-((Tert-butoxycarbonyl)methyl)-[1,2,4]triazolo[4,3-b]pyridazine-6-carboxylic acid | HCID 67503374 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Ammonium hydroxide methanol | HCID 21894508 | 1% |
| Product | Tert-butyl (6-carbamoyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate | HCID 57691087 | 52% |
Reaction Steps
tert-butyl (6-carbamoyl-[1,2,4]-triazolo[4,3-b]pyridazin-3-yl)methylcarbamate. In a 10 mL round bottom flask under N2 were dissolved 3-((tert-butoxycarbonyl)methyl)-[1,2,4]triazolo[4,3-b]pyridazine-6-carboxylic acid (250 mg, 852 μmol), HATU (389 mg, 1023 μmol), triethylamine (356 μl, 2557 μmol) in 1.5 mL of DMF then was treated with a (92 μl, 4262 μmol) and stirred at rt. After 2 h the reaction mixture based on LC-MS was concentrated under reduced pressure and then purified by MPLC (ISCO) with DCM:MeOH+NH4OH (1%) 100:0 to 90:10 to afforded tert-butyl (6-carbamoyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (129 mg, 52% yield). MS m/z=293.2 [M+1]+. Calc'd for C12H16N6O3: 292.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08524900B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-9d396820e0f44ba6b847db7190ceb2e2 |
| Source note | uspto-grants-2013_09 |