Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | 3-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one | HCID 51030598 | — |
| Reactant | HCID 67067735 | HCID 67067735 | — |
| Reactant | HCID 67067926 | HCID 67067926 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 50992440 | HCID 50992440 | 48% |
Reaction Steps
Following the procedure for 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, a mixture of (1-{4-[4-chloro-6-oxo-8-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1,6-dihydro-chromeno[7,8-d]imidazol-7-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester and (1-{4-[4-chloro-6-oxo-8-phenyl-3-(4-trimethylsilanyl-butyl)-3,6-dihydro-chromeno[7,8-d]imidazol-7-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester (46 mg, 0.07 mmol) were reacted to give crude product. This residue was subjected to flash chromatography [SiO2, gradient 0 to 15% MeOH (2 M NH3) in DCM] to furnish the title compound as a white solid (15 mg, 48%). LCMS (Method E): RT=2.96 min, [M+H]*=442/444. 1H NMR (400 MHz, DMSO-d6): 8.33 (s, 1H), 7.87 (s, 1H), 7.45-7.41 (m, 2H), 7.39-7.35 (m, 2H), 7.32-7.27 (m, 1H), 7.22-7.16 (m, 4H), 2.59-2.50 (m, 2H), 2.31-2.22 (m, 2H), 2.12-2.00 (m, 1H), 1.80-1.69 (m, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08546376B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-90ce5284398b4ae4a1299b67e7796e4b |
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| Source note | uspto-grants-2013_10 |
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