HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 117843009, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-Boc-Azetidine-3-carboxylic acid | HCID 2755981 | — |
| 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 | 2-Bromo-5-chloroaniline | HCID 11310276 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 117843009 | HCID 117843009 | 74% |
Reaction Steps
HATU (980 mg, 2.58 mmol) was added to a mixture of 2-bromo-5-chloroaniline (352 mg, 1.7 mmol) and 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid (402 mg, 2 mmol) in Acetonitrile (8 mL) at room temperature followed by DIPEA (0.74 mL, 4.26 mmol). After stifling overnight, reaction mixture was concentrated under reduced pressure and resulting residue was purified via silica gel column chromatography (0-50% ethyl acetate/hexanes) to yield tert-butyl 3-((2-bromo-5-chlorophenyl)carbamoyl)azetidine-1-carboxylate 7.56 (490 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C15H19BrClN2O3: 389.02; found: 389.57.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09376441B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-0083b5d2ea194a498574c15e0ee63ab7 |
| Source note | uspto-grants-2016_06 |