Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Calciumoxide | HCID 6850728 | — |
| Reactant | HCID 178507835 | HCID 178507835 | — |
| Reactant | HCID 178517815 | HCID 178517815 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 178507834 | HCID 178507834 | 63.2% |
Reaction Steps
A mixture of intermediate 15 (2 g), 2-chloro-4-hydroxyquinazoline (1.9 g), N,N-dimethylacetamide (0.3 ml) and calciumoxide (0.4 g) was stirred for 1 hour at 140° C., then cooled and partitioned between water and DCM (+methanol). The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 95/5). The desired fractions were collected and the solvent was evaporated. The residue was suspended in DIPE, filtered off, then dried (vacuum, 60° C.), yielding 1.4 g (50%) [1-[2-[(1,4-dihydro-4-oxo-2-quinazolinyl)amino]ethyl]-4-piperidinyl]methyl 8-amino-7-chloro-2,3-dihydro-1,4-benzodioxin-5-carboxylate (compound 19).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06800628B2 |
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| Source dataset | uspto-grants-2004_10 |
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| ORD ID | ord-f8db95eef98a49bd9f22eab8215319b9 |
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| Source note | uspto-grants-2004_10 |
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