HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-Bromofuran-3-carboxamide → [5-(4-Carbamoyl-furan-2-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-Bromofuran-3-carboxamide | HCID 10821494 | — |
| Reactant | (4-Morpholin-4-yl-phenyl)-(5-tributylstannanyl-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-carbamic acid tert-butyl ester | HCID 67047357 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Ammonia | HCID 222 | — |
| Product | [5-(4-Carbamoyl-furan-2-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester | HCID 67047322 | 65.6% |
Reaction Steps
This compound may be prepared using methods as described for Compound 35, step 3 using (4-morpholin-4-yl-phenyl)-(5-tributylstannanyl-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-carbamic acid tert-butyl ester (137 mg, 0.199 mmol), 5-bromo-furan-3-carboxamide (76 mg, 0.4 mmol) and Pd(PPh3)4 (23 mg, 0.020 mmol) in DMF (1 mL). Purification of the reaction mixture eluting with 98:2 DCM:MeOH and 96:4 DCM:NH3 (7M in MeOH) affords the title compound (33 mg, 33%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07501411B2 |
| Source dataset | uspto-grants-2009_03 |
| ORD ID | ord-4682667b785a4aff8b0f28ad39cf080c |
| Source note | uspto-grants-2009_03 |