Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-(4-Methoxyphenyl)cyclopropane-1-carboxylic acid | HCID 85575 | — |
| Reactant | 5-(2-Chloro-benzyl)-thiazol-2-ylamine | HCID 727745 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 11538561 | HCID 11538561 | 54.4% |
Reaction Steps
5-(2-Chloro-benzyl)-thiazol-2-ylamine (0.250 g, 1.11 mmol) and 1-(4-methoxy-phenyl)-cyclopropanecarboxylic acid (0.213 g, 1.11 mmol) were dissolved in acetonitrile (20 mL) containing triethylamine (0.28 mL, 2.0 mmol). O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 0.494 g, 1.3 mmol) was added and the solution was allowed to stir for 16 hours. The crude product was evaporated to dryness and purified by column chromatography on silica gel using a gradient of 5-40% ethyl acetate in hexanes. The pure fractions were combined and evaporated to dryness to yield a white solid (0.2408 g, 0.6036 mmol, 54.4%). ESI-MS m/z calc. 398.1. found 399.0 (M+1)+. Retention time of 3.77 minutes. 1H NMR (400 MHz, CD3CN) d 1.21 (q, J=3.6 Hz, 2H), 1.59 (q, J=3.6 Hz, 2H), 3.78 (s, 3H), 4.19 (s, 2H), 6.88-6.96 (m, 2H), 7.07 (s, 1H), 7.23-7.46 (m, 6H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08759335B2 |
|---|
| Source dataset | uspto-grants-2014_06 |
|---|
| ORD ID | ord-981df365e13c4d1f84f48ff2a8c06cee |
|---|
| Source note | uspto-grants-2014_06 |
|---|
