Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanolamine | HCID 700 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | HCID 59583660 | HCID 59583660 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 42606565 | HCID 42606565 | 30% |
Reaction Steps
A mixture of 2-[({1-[(3,4-dichlorophenyl)methyl]-1H-1,2,3-triazol-4-yl}carbonyl)amino]-1,3-thiazole-5-carboxylic acid (Intermediate 14) (0.18 g, 0.45 mmol), 2-aminoethanol (32 μL, 1.2 eq), HATU (0.22 g, 1.3 eq) and DIPEA (100 μL, 1.3 eq) in DMF (20 mL) was stirred at 40° C. for 48 hours. The solvent was evaporated and the residue was washed with water and extracted with DCM. The insoluble compound was filtered and washed with a mixture of acetonitrile/methanol 80/20 and then purified by flash chromatography eluting with DCM/MeOH (95/5) to give the title compound as a white solid (60 mg, 30%). HRMS calculated for C16H14Cl2N6O3S (M+H)+441.0303, found: 441.0339, Rt: 2.39 min. MP: 274.8° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08207204B2 |
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| Source dataset | uspto-grants-2012_06 |
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| ORD ID | ord-cff75d404a2f4cb9be46616ae4ec1340 |
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| Source note | uspto-grants-2012_06 |
|---|