HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 3,3,3-trifluoro-1-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)propan-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4,4,4-Trifluorobutanoic acid | HCID 2777085 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 6-Phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole | HCID 86691988 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3,3,3-trifluoro-1-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)propan-1-one | HCID 86692002 | — |
Reaction Steps
A mixture of 6-phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole (prepared as described in Example 2 above, 66 mg, 0.17 mmol), 3-trifluoromethylpropionic acid (23 mg, 0.18 mmol), HATU (75 mg, 0.2 mmol) and triethylamine (87 mg, 0.86 mmol) in THF (7 mL) was stirred overnight. The resulting mixture was partitioned between etyl acetate and water, and the organic layer was washed sequentially with NaHCO3 (sat'd) and brine, then dried (Na2SO4) and concentrated. The residue was purified by reverse-phase chromatography (CH3CN/H2O-TFA) to yield 3,3,3-trifluoro-1-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)propan-1-one.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09216998B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-5ce1aff59e324a00a573d6648955ace1 |
| Source note | uspto-grants-2015_12 |