Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Chloro-5-pyridinesulfonyl chloride | HCID 2792792 | — |
| Reactant | 1,1-Dimethylethyl (2S)-2-methyl-4-{[4-(methylamino)phenyl]methyl}-1-piperazinecarboxylate | HCID 59262131 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59532414 | HCID 59532414 | 88.1% |
Reaction Steps
D3 (500 mg, 1.57 mmol) and 2-chloro-pyridine-5-sulfonyl chloride (330 mg, 1.57 mmol) were combined in DCM (10 mL) under Ar. Triethylamine (0.44 mL, 3.13 mmol) was added and the solution stirred overnight. The solution was diluted with DCM and washed with water. The water layer was re-extracted with DCM. The combined organic layers were washed with brine, dried and concentrated. The crude product was purified by column chromatography. Elution with 0-50% Et2O/petroleum ether yielded the product as a white foam (685 mg), δH (CDCl3, 400 MHz): 1.24 (3H, d), 1.46 (9H, s), 2.01 (1H, m), 2.16 (1H, m), 2.56 (1H, d), 2.73 (1H, d), 3.10 (1H, m), 3.22 (3H, s), 3.40-3.50 (2H, AB), 3.81 (1H, d), 4.20 (1H, br.s), 7.05 (2H, d), 7.31 (2H, d), 7.42 (1H, d), 7.74 (1H, dd), 8.54 (1H, d). MS (ES+): MH+ 495.1/497.1
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07964597B2 |
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| Source dataset | uspto-grants-2011_06 |
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| ORD ID | ord-56154e1dcb264f0295dd67099f3f99a1 |
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| Source note | uspto-grants-2011_06 |
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