HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-(2-Aminoethyl)piperidine → n-{4-[4-Amino-7-((1e)-3-oxo-3-{[2-(1-piperidinyl)ethyl]amino}-1-propenyl)thieno[3,2-c]pyridin-3-yl]-2-methoxyphenyl}-1-methyl-1h-indole-2-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-(2-Aminoethyl)piperidine | HCID 33944 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | (2e)-3-[4-Amino-3-(3-methoxy-4-{[(1-methyl-1h-indol-2-yl)carbonyl]amino}phenyl)thieno[3,2-c]pyridin-7-yl]acrylic acid | HCID 18450569 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Product | n-{4-[4-Amino-7-((1e)-3-oxo-3-{[2-(1-piperidinyl)ethyl]amino}-1-propenyl)thieno[3,2-c]pyridin-3-yl]-2-methoxyphenyl}-1-methyl-1h-indole-2-carboxamide | HCID 18451052 | 77.3% |
Reaction Steps
A mixture of Example 271 (30.6 mg, 0.044 mmol), N,N-diisopropylethylamine (35 μL, 0.20 mmol), 2-piperidin-1-ylethylamine (14.3 μL, 0.10 mmol), and DMF (1 mL) was treated sequentially with 0.5M (0.09 mL) of HBTU in DMF and 0.5M (0.09 mL) of HOBT in DMF. The reaction was stirred for 24 hours at ambient temperature and partitioned between 1N NaOH and ethyl acetate. The combined extracts were dried (Na2SO4), filtered, and concentrated to provide the desired product (20.4 mg, 0.034 mmol). LCMS m/e 609.2; retention time: 2.93 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07737160B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-585d77817bde4fd294a8c4e590ce7589 |
| Source note | uspto-grants-2010_06 |