Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyclobutylamine | HCID 75645 | — |
| 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 | 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrazole-4-carboxylic acid | HCID 57937295 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 23660107 | HCID 23660107 | 47% |
Reaction Steps
Following the same procedure in Example 24, Step A, using cyclobutylamine (13 uL, 10 mg, 0.15 mmol), DIPEA (28 uL, 21 mg, 0.16 mmol), 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrazole-4-carboxylic acid (0.073 mmol) and HATU (44 mg, 0.12 mmol) in DMF (2.5 mL). The crude product was purified by MPLC using Hex/EtOAc (1:2) on silica gel to give 17 mg (47%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.40-1.56 (m, 4 H), 1.58 (s, 9 H), 1.67-1.79 (m, 2 H), 1.96-2.09 (m, 2 H), 2.22-2.34 (m, 3 H), 3.25-3.34 (m, 2 H), 3.83-3.94 (m, 2 H), 4.34-4.39 (m, 1 H), 4.41 (d, J=7.62 Hz, 2 H), 7.90 (d, J=8.6 Hz, 1 H), 7.97 (dd, J=8.8, 1.8 Hz, 1 H), 8.04 (d, J=0.59 Hz, 1 H), 8.33 (d, J=1.37 Hz, 1 H), 8.77 (d, J=0.59 Hz, 1 H); MS (ESI) (M+H)+=499.8; Anal. Calcd for C25H33N5O4S+0.70 TFA+0.30 EtOAc+0.20H2O (613.09): C, 54.66; H, 6.00; N, 11.42. Found: C, 54.63; H, 5.95; N, 11.51.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07615642B2 |
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| Source dataset | uspto-grants-2009_11 |
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| ORD ID | ord-4f54a0b43ab4430692f0c7e37fe5f3cf |
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| Source note | uspto-grants-2009_11 |
|---|
