Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Isonicotinic Acid | HCID 5922 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| 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 | HCID 67988152 | HCID 67988152 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 67988170 | HCID 67988170 | — |
Reaction Steps
4-pyridinecarboxylic acid (30.3 mg, 0.247 mmol) was dissolve in N,N-Dimethylformamide (DMF) (3 mL) under argon flow. HATU (86 mg, 0.226 mmol) was added. After 30 minutes of stirring, 1-[5-bromo-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-N-methyl-4-piperidinamine D25 (100 mg) was added. After 20 minutes of stirring, DIPEA (0.144 mL, 0.822 mmol) was added. The mixture was stirred at room temperature under argon flow for all the night. DCM (10 mL) has been added to the mixture. The work-up has been done with 2×10 mL of Na2CO3, 10 mL of brine. The organic layer was filtrated by a phase separator and put under vacuo to remove the solvent. The crude material was purified by silica chromatography eluting by a gradiant of solvent: 0-5% of MeOH in DCM. The fractions were collected and the solvent has been evaporated to give the product D26 in 41 mg. LCMS [M+H]+555.01/557.03 g 2.64 min (5 min run)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09045485B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-3299c800fa104b89b1d12a93d3a8321b |
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| Source note | uspto-grants-2015_06 |
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