HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Chlorobenzoic Acid → 3-Chloro-N-{1-(1,4-dioxa-8-azaspiro[4.5]dec-8-ylcarbonyl)-5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}benzenecarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Chlorobenzoic Acid | HCID 447 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| 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 | {3-Amino-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)methanone hydrochloride | HCID 66760651 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-Chloro-N-{1-(1,4-dioxa-8-azaspiro[4.5]dec-8-ylcarbonyl)-5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}benzenecarboxamide | HCID 66761061 | — |
Reaction Steps
0.59 ml (3.38 mmol) of N,N′-diisopropylethylamine and 248 mg (1.58 mmol) of 3-chlorobenzoic acid were added to a solution of the compound from Example 62A (500 mg, 1.06 mmol) in N,N′-dimethylformamide (18 ml). After addition of 522 mg (1.37 mmol) of HATU, the mixture was stirred at RT overnight. The reaction mixture was purified directly by preparative HPLC(RP18 column; acetonitrile/water gradient). Yield: 414 mg (67% of theory)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08987248B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-cb14622e14d94ee59f538435f4589064 |
| Source note | uspto-grants-2015_03 |