HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclopropanemethanamine → 1-(Cyclopropylmethyl)-3-(1-(1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-yl)-1H-indazol-6-yl)urea
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclopropanemethanamine | HCID 75646 | — |
| Reactant | 4-Nitrophenyl chloroformate | HCID 82129 | — |
| Reactant | 2-(4-((4-(6-Amino-1H-indazol-1-yl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol | HCID 86671000 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-(Cyclopropylmethyl)-3-(1-(1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-yl)-1H-indazol-6-yl)urea | HCID 86671001 | 77% |
Reaction Steps
2-(4-((4-(6-Amino-1H-indazol-1-yl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.212 mmol, 0.1 g) and 4-nitrophenyl carbonochloridate (0.212 mmol, 0.043 g) were combined and stirred in dichloromethane (2 mL) for 1 hour. Cyclopropylmethanamine (0.423 mmol, 0.037 mL, 0.030 g) was added and the reaction stirred at room temperature for 2 hours. The organic was washed with water and dried over sodium sulfate. The solvent was removed and the resulting residue was purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 6% methanol/dichloromethane) to afford the title compound (93 mg). MS (ESI) m/z 570.0 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09108939B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-cc2af130838d41e79e6e16afafc9a829 |
| Source note | uspto-grants-2015_08 |