Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 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 | 5′-[(Cyclopropylamino)carbonyl]-2′-methyl[1,1′-biphenyl]-4-carboxylic acid | HCID 11220151 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 69512979 | HCID 69512979 | — |
Reaction Steps
HATU (65 mg, 0.17 mmol) was added to a solution of {3′-[(cyclopropylamino)carbonyl]-6′-methyl-biphen-4-yl} carboxylic acid (50 mg, 0.17 mmol) in DMF (2 ml). After 5 minutes HOBT (23 mg, 0.17 mmol), amine (0.17 mmol) and DIPEA (0.087 ml, 0.51 mmol) were added and the reaction mixture stirred at room temperature under nitrogen for 18 hours. Ethyl acetate (50 ml) and hydrochloric acid (1M, 50 ml) were added and the layers separated. The organic layer was washed with aqueous sodium carbonate (1M, 50 ml), brine (25 ml), dried (magnesium sulphate) and solvent removed in vacuo. The crude material was purified by SPE cartridge (Si, 5 g) eluting with DCM:ethanol:ammonia 400:8:1, then, ethyl acetate, acetonitrile, acetone and ethanol to yield the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07208629B2 |
|---|
| Source dataset | uspto-grants-2007_04 |
|---|
| ORD ID | ord-478982feed204563a96aa9fbd2aa8bfc |
|---|
| Source note | uspto-grants-2007_04 |
|---|
