Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrogen Bromide | HCID 260 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | 1-(3-(5-(3-Chloro-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-ethylbenzyl)azetidine-3-carboxylic acid | HCID 58494012 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 86659016 | HCID 86659016 | — |
Reaction Steps
1-{[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylphenyl]methyl}-3-azetidinecarboxylic acid (50 mg, 0.106 mmol) was added to a mixture of THF (2 mL), water (0.6 mL) and ACN (1 mL), a suspension was obtained to which was added HBr solution (0.016 mL, 40%, wt). A clear solution was obtained and stirred for 30 min at rt. Solvent was removed under the reduced pressure and dried in vacuum to give 3-carboxy-1-(3-(5-(3-chloro-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-ethylbenzyl)azetidin-1-ium bromide (56 mg) as pale yellow solid. δH (DMSO-d6, 600 MHz): 1.08 (3H, t), 1.35 (6H, m), 2.92 (2H, m), 3.67 (1H, m), 4.34 (4H, m), 4.61 (2H, m), 4.85 (1H, dt), 7.39 (1H, d), 7.48 (1H, m), 7.64 (2H, m), 7.97 (1H, d), 8.10 (1H, d), 10.25 (1H, s), 13.17 (1H, d).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08389508B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-85d8343f18eb4a74a6bfb428b7763c7c |
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| Source note | uspto-grants-2013_03 |
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