Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | 2-Chloropyrimidine-5-carboxylic acid | HCID 11094906 | — |
| Reactant | (2-(Trifluoromethyl)-1h-indol-5-yl)methanamine | HCID 58126817 | — |
| Catalyst | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 58126827 | HCID 58126827 | 56.5% |
Reaction Steps
2-Chloro-pyrimidine-5-Carboxylic acid (209 mg, 1.317 mmol) was stirred in dichloromethane (20 ml). Oxalyl chloride (0.210 ml, 2.394 mmol) then DMF (4.63 μl, 0.060 mmol) was added. The reaction mixture was then left to stir for 2 h under Argon gas. The reaction mixture was then evaporated to dryness and the resulting residues were then dissolved in dichloromethane (20 ml). A solution of {[2-(trifluoromethyl)-1H-indol-5-yl]methyl}amine (Intermediate 4, 300 mg, 1.197 mmol) in DCM (10 mL) was added then triethylamine (0.500 ml, 3.59 mmol) was added. The reaction mixture was then left to stir at room temperature for 24 h. The reaction mixture was evaporated to dryness. The resulting residues where then partitioned between 2M HCl (50 ml) and ethyl acetate (50 ml). The organic layer was collected, dried (MgSO4), filtered and the solvent was removed. The resulting residues where then purified on the MDAP to give the title compound (240 mg);
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08377941B2 |
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| Source dataset | uspto-grants-2013_02 |
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| ORD ID | ord-539a5be6b2534249aa24f7b10d2bbacb |
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| Source note | uspto-grants-2013_02 |
|---|