Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Glycine | HCID 750 | — |
| Reactant | Sodium methanolate methanol | HCID 23694274 | — |
| Reactant | HCID 68427909 | HCID 68427909 | — |
| Product | HCID 24757242 | HCID 24757242 | 75.7% |
Reaction Steps
A mixture of 7-hydroxy-2-pyridin-2-yl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (43 mg, 0.14 mmol) and glycine (214 mg, 2.86 mmol) in 0.5 M sodium methoxide/methanol (5.4 mL, 1.29 mmol) was refluxed for 2 days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water and extracted with methyl tert-butyl ether (2×25 mL). The remaining aqueous layer was acidified to pH=3 with 1N HCl (4 mL). The precipitate was filtered, washed with water and dried in vacuo to give the title compound as a white solid (35 mg): 1H NMR (DMSO-d6, 200 MHz): δ=13.16 (br s, 1H), 9.47 (br s, 1H), 8.92 (s, 1H), 8.75 (d, J=4.3 Hz, 1H), 8.32 (d, J=7.8, 1H), 8.05 (m, 1H), 7.65 (m, 1H), 4.03 (d, J=6.3 Hz, 2H); MS: (+) m/z 331.00 (M+1); (−) m/z 329.00 (M−1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07696223B2 |
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| Source dataset | uspto-grants-2010_04 |
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| ORD ID | ord-1c2789129678434db326dc298b039196 |
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| Source note | uspto-grants-2010_04 |
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