Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | HCID 68291931 | HCID 68291931 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68349424 | HCID 68349424 | 35.5% |
Reaction Steps
To a solution of (R)-3-(3-carbamoyl-4-(1-cyclopropylethylamino) pyrrolo[1,2-b]pyridazin-6-yl)benzoic acid (Example 85, 15 mg, 0.041 mmol), dimethylamine (0.021 mL, 0.041 mmol) and triethylamine (8.61 μl, 0.062 mmol) in DMF (0.5 mL) was added BOP (18.21 mg, 0.041 mmol) which was stirred at 23° C. for 30 minutes. The reaction mixture was purified by reverse-phase preparative HPLC (condition C) to yield the title compound (5.7 mg, 35%). HPLC (condition H): retention time=1.47 minutes. LC/MS (M+H)+=392.3. 1H NMR (500 MHz, MeOD) δ ppm 8.06 (1 H, s), 7.86 (1 H, d, J=1.9 Hz), 7.67-7.71 (1 H, m), 7.64 (1 H, t, J=1.4 Hz), 7.45 (1 H, t, J=7.6 Hz), 7.24-7.27 (1 H, m), 7.09 (1 H, d, J=1.7 Hz), 4.01-4.09 (1H, m), 3.13 (3 H, s), 3.04 (3 H, s), 1.44 (3 H, d, J=6.4 Hz), 1.09-1.18 (1 H, m), 0.57 (2H, dd, J=13.5, 8.7 Hz), 0.34-0.41 (2 H, m).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09221826B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-1c9ce810a1804104a789fbac1341d4d4 |
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| Source note | uspto-grants-2015_12 |
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