Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | HCID 67253348 | HCID 67253348 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67252926 | HCID 67252926 | 56% |
Reaction Steps
A solution of {6-[2-(3-tert-butoxycarbonylamino-propylamino)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid (0.27 g, 0.57 mmol) in dioxane (7 mL) was treated with 4N HCl in dioxane (2 mL) at room temperature and stirred for 3 hours at room temperature. The precipitated solid was collected by vacuum filtration, dissolved in water and lyophilized to give {6-[2-(3-amino-propylamino)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid hydrochloride salt as a yellow solid (0.12 g, 56%). 1H NMR (400 MHz, DMSO-d6) δ 8.57 (br s, 1H), 8.37-8.10 (br m, 1H), 7.94 (br m, 3H), 7.50-7.25 (br m, 1H), 7.20-7.05 (br m, 1H), 6.47 (br s, 1H), 5.54 (d, J=9.38 Hz, 1H), 3.36 (br m, 1H), 3.20-3.00 (m, 2H), 2.80 ((m, 1H), 2.67 (m, 1H), 2.33 (s, 3H), 2.20-2.07 (m, 1H), 1.95-1.60 (m, 2H). MS (ESI) m/z: 371 [M−1].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08343944B2 |
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| Source dataset | uspto-grants-2013_01 |
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| ORD ID | ord-9f6119b28314467f81c7084695471a64 |
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| Source note | uspto-grants-2013_01 |
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