HuagongsheHuagongshe Chemistry Print Report · For research reference only
Carbamate → 1-(4-(4-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(methylsulfonylmethyl)pyrimidin-2-yl)phenyl)-3-(4-(piperazin-1-yl)phenyl)urea
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Carbamate | HCID 276 | — |
| Reactant | Urea | HCID 1176 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | 4-(4-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(methylsulfonylmethyl)pyrimidin-2-yl)aniline | HCID 66750277 | — |
| Reactant | HCID 67607491 | HCID 67607491 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-(4-(4-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(methylsulfonylmethyl)pyrimidin-2-yl)phenyl)-3-(4-(piperazin-1-yl)phenyl)urea | HCID 49764385 | — |
Reaction Steps
tert-Butyl 4-(4-(3-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(methylsulfonylmethyl)pyrimidin-2-yl)phenyl)ureido)phenyl)piperazine-1-carboxylate was obtained according to the general procedure for formation of urea or carbamate compounds from 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(methylsulfonylmethyl)pyrimidin-2-yl)aniline (44). Removal of the Boc group in tert-butyl 4-(4-(3-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(methylsulfonylmethyl)pyrimidin-2-yl)phenyl)ureido)phenyl)piperazine-1-carboxylate (85.2 mg, 0.126 mmoles) by treatment with trifluoroacetic acid in dichloromethane gave the title compound. Yield: 70.0 mg (38% over 2 steps). RT 1.64, M+H=578.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08835429B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-edc050be6d4743f0b065629e67417aa7 |
| Source note | uspto-grants-2014_09 |