Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 7H-Pyrrolo(2,3-d)pyrimidine, 4-chloro- | HCID 5356682 | — |
| Reactant | HCID 45139442 | HCID 45139442 | — |
| Solvent | 1-Butanol | HCID 263 | — |
| Product | HCID 45141621 | HCID 45141621 | 69% |
Reaction Steps
A degassed mixture of crude N-(4-amino-piperidin-4-ylmethyl)-4-chloro-benzamide dihydrochloride (6.1 mg), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (2.6 mg, 0.016 mmol), triethylamine (16 μL, 0.09 mmol) and n-butanol (0.3 mL) was stirred at 100° C. for 17 hours. The solvents were concentrated. The crude mixture was first purified on an SCX-II acidic resin, eluting with methanol then 2M ammonia-methanol, and then by preparative TLC, eluting with 15% methanol-dichloromethane, to give N-[4-amino-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperidin-4-ylmethyl]-4-chloro-benzamide (3.3 mg, 0.009 mmol, 69% over 2 steps). LC-MS (LCT2) m/z 385 [M+H+], Rt 2.58 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08809336B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-669dde179be448cc9f850854c949d583 |
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| Source note | uspto-grants-2014_08 |
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