HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 2-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid (2-hydroxy-2-methyl-propyl)-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Propanol, 1-amino-2-methyl- | HCID 95102 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | 2-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid | HCID 66643669 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid (2-hydroxy-2-methyl-propyl)-amide | HCID 49782038 | 56% |
Reaction Steps
To a solution of 2-[2-(3-butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid (80 mg, 0.26 mmol) in DMF (4 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (92 mg, 0.29 mmol), N,N-diisopropyl ethyl amine (168 mg, 1.3 mmol) and 1-amino-2-methyl-propan-2-ol (25 mg, 0.29 mmol). The resulting reaction mixture was stirred for 15 h and then evaporated. Purification by chromatography (silica, 0 to 10% methanol in dichloromethane) afforded the title compound (55 mg, 56%) as a colourless oil MS: m/e=380.4 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08178522B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-5fab0bdf588f42158c32c0ab72bef736 |
| Source note | uspto-grants-2012_05 |