HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → tert-butyl 2-(4-(5-(2-amino-5-methoxyphenylcarbamoyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)piperidin-1-yl)ethyl(methyl)carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 4-Methoxybenzene-1,2-diamine dihydrochloride | HCID 3085161 | — |
| Reactant | 1-(1-(2-(tert-butoxycarbonyl(methyl)amino)ethyl)piperidin-4-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid | HCID 59843214 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | tert-butyl 2-(4-(5-(2-amino-5-methoxyphenylcarbamoyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)piperidin-1-yl)ethyl(methyl)carbamate | HCID 59843143 | 84% |
Reaction Steps
To a stirred solution of 96 (160 mg, 0.381 mmol) in DMF (1.903 mL) was added EDC (88 mg, 0.457 mmol), HOBT (69.9 mg, 0.457 mmol) followed by 4-Methoxy-o-phenylenediamine dihydrochloride (73.1 mg, 0.419 mmol). The mixture was stirred for 16 h at room temperature. After the usual work-up, the residue was purified via Biotage (5% to 15% MeOH/CH2Cl2; 12M column) to afford 106 (172 mg, 84% yield) as yellow oil. LRMS (ESI): calc. 540.6; found 541.4 (MH)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08338437B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-6882ce41f0ae4569921c4bafbdc096b7 |
| Source note | uspto-grants-2012_12 |