Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | HCID 59168325 | HCID 59168325 | — |
| Catalyst | Acetic Acid | HCID 176 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59168336 | HCID 59168336 | — |
Reaction Steps
To a solution of 2-(5-chloro-6-((R)-4-(6-(3-chloro-4-fluorophenyl)-2-((R)-2-methylpyrrolidin-1-yl)pyrimidin-4-yl)-3-methylpiperazin-1-yl)pyridin-3-yl)acetaldehyde (64 mg, 0.118 mmol) in DCE, add dimethylamine (3.87M in THF, 40 μL) followed by 1 drop of HOAc. Stir the mixture overnight, and then dilute with DCM and wash (2×) with 10% NaOH solution. Concentrate under reduced pressure and add EtOAc, followed by a solution of HCl in ether. Concentrate and triturate the hydrochloride salt with fresh EtOAc to afford the title compound. 1H NMR (400 MHz, CDCl3): δ1.31 (d, 3H, J=6.23 Hz, CH3), 1.39 (d, 3H, J=6.6 Hz, CH3), 1.68 (m, 1H), 1.91 (m, 1H), 2.05 (m, 5H), 2.68 (s, 6H, N(CH3)2), 2.9-3.1 (m, 4H), 3.65 (m, 1H), 3.63-3.9 (m, 4H), 4.34 (m, 2H), 4.67 (br s, 1H), 6.20 (s, 1H), 7.18 (t, 1H), 7.55 (s, 1H), 7.88 (m, 1H), 8.06 (s, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08334382B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-72364a4f7ba3455a948e54ede3676cb0 |
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| Source note | uspto-grants-2012_12 |
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