HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → [(R)-3-(6-Chloro-benzooxazol-2-ylamino)-pyrrolidin-1-yl]-o-tolyl-methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 2-Methylbenzoic acid | HCID 8373 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | (6-Chloro-benzooxazol-2-yl)-pyrrolidin-3-yl-amine | HCID 57748894 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | [(R)-3-(6-Chloro-benzooxazol-2-ylamino)-pyrrolidin-1-yl]-o-tolyl-methanone | HCID 57748968 | 61.4% |
Reaction Steps
A mixture of 32.9 mg (0.12 mmol) (6-Chloro-benzooxazol-2-yl)-pyrrolidin-3-yl-amine; hydrochloride, 19.6 mg (0.144 mmol) 2-methyl-benzoic acid, 53.9 mg (0.168 mmol) TBTU and 77.5 mg (0.6 mmol) DIPEA in 2 mL DMF was stirred at room temperature for 16 h. The mixture was concentrated, taken up in methanol and formic acid and subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid. The product containing fractions were evaporated to yield 26.2 mg (61%) of the title compound. (MH+) 356.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07897627B2 |
| Source dataset | uspto-grants-2011_03 |
| ORD ID | ord-319c5c7a371c41038d972afcf6a6310f |
| Source note | uspto-grants-2011_03 |