Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 3-Chloro-2-fluoroaniline | HCID 75014 | — |
| Reactant | HCID 86624373 | HCID 86624373 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 68521486 | HCID 68521486 | 66% |
Reaction Steps
HCl (1.0 ml, 4M solution in dioxane) was added to 4-chloro-7-methoxy-6-[(3S)-1-(tert-butoxycarbonyl)piperidin-3-yloxy]quinazoline (0.786 g) and 3-chloro-2-fluoroaniline (0.304 g) dissolved in acetonitrile (25 ml). The mixture was heated to 60° C. for 2 hours, cooled and the precipitate collected to give 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-[(3S)-piperidin-3-yloxy]quinazoline hydrochloride as a white solid (0.577 g, 66%); 1H NMR Spectrum: (DMSOd6) 1.70-1.95 (m, 2H), 1.95-2.10 (m, 1H); 2.10-2.25 (m, 1H), 2.95-3.10 (m, 1H), 3.10-3.30 (m, 2H), 3.45-3.65 (m, 1H); 4.03 (s, 3H); 4.95-5.10 (m, 1H); 7.30-7.45 (m, 1H); 7.45-7.60 (m, 2H); 7.60-7.73 (m, 1H), 8.85 (s, 1H); 8.90 (s, 1H); 9.15 (bs, 2H); 12.3 (bs, 1H); Mass Spectrum: (M+H): 403.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08399667B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-b6de745de2614a7087c58c0f0e1f0717 |
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| Source note | uspto-grants-2013_03 |
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