Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylamine | HCID 6341 | — |
| 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 23660108 | HCID 23660108 | 49.2% |
Reaction Steps
Following the same procedure in Example 24, Step A, using ethylamine (73 uL, 2.0 M in THF, 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 (48%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.15 (t, J=7.23 Hz, 3 H), 1.40-1.57 (m, 4 H), 1.59 (s, 9H), 2.21-2.41 (m, 1 H), 2.79 (s, 1 H), 3.29-3.35 (m, 4 H), 3.84-3.95 (m, 2 H), 4.41 (d, J=7.42 Hz, 2 H), 7.91 (d, J=9.0 Hz, 1 H), 7.98 (dd, J=9.0, 1.7 Hz, 1 H), 8.03 (s, 1 H), 8.33 (d, J=1.56 Hz, 1 H), 8.74 (s, 1 H); MS (ESI) (M+H)+=474.0; Anal. Calcd for C23H31N5O4S+0.70 TFA+0.30 EtOAc+0.40H2O (590.66): C, 52.67; H, 5.96; N, 11.86. Found: C, 52.63; H, 5.99; N, 11.81.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07615642B2 |
|---|
| Source dataset | uspto-grants-2009_11 |
|---|
| ORD ID | ord-12a9ad25eb764498979819c93226757c |
|---|
| Source note | uspto-grants-2009_11 |
|---|
