HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclopropanemethanamine → 4-Amino-6-{4-[1-[2-(cyclopropylmethyl-amino)-ethyl]-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclopropanemethanamine | HCID 75646 | — |
| Reactant | Methanesulfonic acid 2-[2-[1-(6-amino-5-cyano-pyrimidin-4-yl)-piperidin-4-yl]-4-(4-fluoro-3-trifluoromethyl-phenyl)-imidazol-1-yl]-ethyl ester | HCID 89442673 | — |
| Product | 4-Amino-6-{4-[1-[2-(cyclopropylmethyl-amino)-ethyl]-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbonitrile | HCID 89442547 | 40.3% |
Reaction Steps
The title compound was prepared by stirring methanesulfonic acid 2-[2-[1-(6-amino-5-cyano-pyrimidin-4-yl)-piperidin-4-yl]-4-(4-fluoro-3-trifluoromethyl-phenyl)-imidazol-1-yl]-ethyl ester (85.0 mg; 0.15 mmol; 1.00 eq) in cyclopropylmethylamine (54.6 mg, 0.77 mmol; 5.0 eq) at ambient temperature. The reaction mixture was purified via flash chromatography using a gradient of 0-10% methanol in dichloromethane to give 4-Amino-6-{4-[1-[2-(cyclopropylmethyl-amino)-ethyl]-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbonitrile (32.7 mg; 0.06 mmol; 40.3%). LC-MS: (M+1=529, obsd.=529).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09145392B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-f8e17c8f542f45d5a0034d17dddd9a46 |
| Source note | uspto-grants-2015_09 |