Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Methylcyclopropanecarboxylic acid | HCID 81326 | — |
| Reactant | 4-(3-Aminobenzyl)-5,6,7,8-tetrahydrophthalazin-1(2h)-one | HCID 59755755 | — |
| Reactant | 2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate Methanaminium | HCID 86621144 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 69042912 | HCID 69042912 | — |
Reaction Steps
A solution of EXAMPLE 89 (20 mg, 0.08 mmol), 1-methylcyclopropanecarboxylic acid (10 mg, 0.096 mmol), HATU (2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium) (38 mg, 0.1 mmol) and triethylamine (20 mg, 0.2 mmol) in dimethylacetamide (2.5 mL) was stirred at room temperature for 18 hours, and concentrated. The residue was dissolved in a 1:1 mixture of dimethylsulfoxide/methanol, and separated by HPLC (Waters Sunfire® C-8 analytical column [Milford, Mass.], 0.1% trifluoroacetic acid/water/CH3CN) to provide the title compound. MS (DCI/NH3) m/z 338 (M+H)+; 1H NMR (500 MHz, D2O/dimethylsulfoxide-d6): δ 0.57-0.69 (m, 2H), 1.02-1.10 (m, 2H), 1.38 (s, 3H), 1.57-1.65 (m, 4H), 2.29-2.44 (m, 4H), 3.87 (s, 2H), 6.89 (d, J=7.63 Hz, 1H), 7.23 (t, J=7.93 Hz, 1H), 7.42 (s, 1H), 7.46 (d, J=8.24 Hz, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08466150B2 |
|---|
| Source dataset | uspto-grants-2013_06 |
|---|
| ORD ID | ord-8f4f6c602bdd485aa4bc5830f70e5e44 |
|---|
| Source note | uspto-grants-2013_06 |
|---|