HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → N,N-Dimethyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-methanamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1-Iodo-4-nitrobenzene | HCID 12495 | — |
| Reactant | Sodium Azide | HCID 33557 | — |
| Reactant | N,N-Dimethylpropargylamine | HCID 81643 | — |
| Reactant | L-Proline | HCID 145742 | — |
| Reactant | 4-{8-[4-(4-Pyridin-2-yl-[1,2,3]triazol-1-yl)-phenylamino]-imidazo[1,2-a]pyrazin-5-yl}-benzamide | HCID 17757332 | — |
| Reactant | sodium (L)-ascorbate | HCID 178519209 | — |
| Catalyst | Copper sulfate pentahydrate | HCID 24463 | — |
| Solvent | (Methanesulfinyl)methane--water (1/1) | HCID 23503278 | — |
| Product | Ammonia | HCID 222 | — |
| Product | N,N-Dimethyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-methanamine | HCID 58228820 | 36% |
Reaction Steps
In the same way as described for Compound 154, step 1 using 1-iodo-4-nitrobenzene (0.498 g, 2.0 mmol), 1-dimethylamino-2-propyne (0.216 mL, 2.00 mmol), L-proline (46.1 mg, 0.40 mmol), Na2CO3 (42.4 mg, 0.40), NaN3 (0.156 g, 2.40 mmol), (+)-sodium-L-ascorbate (39.7 mg, 0.20 mmol), copper(II) sulphate pentahydrate (16.0 mg, 0.10 mmol) in 9:1 DMSO-water (4 mL). The residue is purified on Isolute FlashSilicaII cartridge eluting with 97:3 DCM:NH3 (7M in MeOH), to afford the title compound as a brown solid (0.179 g, 36%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07893058B2 |
| Source dataset | uspto-grants-2011_02 |
| ORD ID | ord-30aa47248b164254b877d907f152d213 |
| Source note | uspto-grants-2011_02 |