Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 2,4-Dichloro-1,3,5-triazine | HCID 17810 | — |
| Reactant | HCID 28172280 | HCID 28172280 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 58964357 | HCID 58964357 | 32.8% |
Reaction Steps
To a solution of 2,4-dichloro-1,3,5-triazine (298 mg, 2.0 mmol) in 4 mL THF and isopropanol(1:1 v:v) at −20° C. was added (R)-2-amino-N-(2,2,2-trifluoroethyl)propanamide (412 mg, 2.0 mmol, 1.0 equiv.), followed by the addition of N,N-isopropyl ethyl amine (516 mg, 4.0 mmol, 2.0 equiv.). The reaction was stirred at −20° C. for 20 minutes then was allowed to warm to room temperature. After 30 minutes, the reaction was poured into ethyl acetate and washed with water. The organic layer was concentrated. The oily residue was purified by chromatography (2:1 hexane/ethyl acetate) to produce 186 mg of (R)-2-(4-chloro-1,3,5-triazin-2-ylamino)-N-(2,2,2-trifluoroethyl)propanamide (compound 1034) (LC/MS: MS+1=284.1, MS−1=282.3, R.T.=1.5 min).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08580802B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-90478b29382645c7938a443e00c471c4 |
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| Source note | uspto-grants-2013_11 |
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