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Diisopropylethylamine → 1-tert-butyl-8-(methylsulfanyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | Sodium Bicarbonate | HCID 516892 | — |
| 反応物 | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| 反応物 | O-(Tetrahydropyran-2-yl)hydroxylamine | HCID 5142091 | — |
| 反応物 | 1-tert-butyl-8-(methylsulfanyl)-1H-pyrazolo[4,3-h]quinazoline-3-carboxylic acid | HCID 67976923 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | 1-tert-butyl-8-(methylsulfanyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide | HCID 86668392 | 50% |
反応手順
1-tert-butyl-8-(methylsulfanyl)-1H-pyrazolo[4,3-h]quinazoline-3-carboxylic acid 40 mg (0.112 mmol) was reacted in dry DMF (2 ml) with O-(tetrahydro-2H-pyran-2-yl)hydroxylamine 25 mg (0.21 mmol), TBTU 70 mg (0.21 mmol) and DIPEA 0.110 ml (1.19 mmol) at room temperature for 3 hours. The reaction was worked up with water, saturated NaHCO3 and extracted with ethyl acetate. The organic phase, dried on Na2SO4, filtered and evaporated, was purified on silica with DCM/EtOAc 7/3 to give 23 mg (50%) of 1-tert-butyl-8-(methylsulfanyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide. LC/MS (m/z): 416.1 [M+H]+, HPLC (254 nm) method 3 Rt 6.94 min.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08541576B2 |
| 出典データセット | uspto-grants-2013_09 |
| ORD ID | ord-9fb976c30e2541bd8939abe6bf1a5a41 |
| 出典メモ | uspto-grants-2013_09 |