Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 68182899 | HCID 68182899 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68182986 | HCID 68182986 | 83% |
Reaction Steps
To a solution of methyl 5-chloro-2-[2-(morpholin-4-yl)-4-oxo-5,6-dihydro-4H-[1,3]thiazolo[5,4-c]azepin-8-yl]benzoate (0.125 g, 0.298 mmol) in THF (3.7 mL) and MeOH (1.2 mL) was added a solution of 1M sodium hydroxide in water (3.66 mL, 3.66 mmol). The solution was stirred at room temperature for 16 hours. The solvents were evaporated and the residue was diluted with water and then added 1N hydrogen chloride aqueous solution until pH 7 was reached. Extracted twice with EA and the combined organic layer was then washed with brine then dried over anhydrous sodium sulfate and concentrated to give the product (0.100 g, 83%) which was used directly in the next step. LCMS: (AA) ES+ 406, 408. 1H NMR (400 MHz, d6-DMSO) δ: 12.79 (s, 1H), 7.86 (t, J=4.9 Hz, 1H), 7.68 (d, J=2.4 Hz, 1H), 7.57 (dd, J=8.2, 2.4 Hz, 1H), 7.32 (d, J=8.2 Hz, 1H), 6.21 (t, J=6.9 Hz, 1H), 3.65-3.55 (m, 6H), 3.30-3.26 (m, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08765746B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-bde469b07b7b413985d9768cbb39e954 |
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| Source note | uspto-grants-2014_07 |
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