Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | HCID 44158703 | HCID 44158703 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67520786 | HCID 67520786 | — |
Reaction Steps
A mixture of (2R,4S)-4-[4-(6-amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-pyrrolidine-2-carboxylic acid (10.00 mg, 0.019 mmol), dimethylamine (0.009 g, 0.2 mmol), TBTU (12.4 mg, 0.0388 mmol), and DMF (1 mL) was charged with DIPEA (0.03 mL, 0.2 mmol) and allowed to stir at rt for 10 min. The solution was used directly for HPLC purification. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a yellow solid. 1H NMR (400 MHz, CD3OD): δ=2.40-2.51 (m, 1H), 2.87 (d, J=6.1 Hz, 1H), 3.04 (s, 3H), 3.09 (s, 3H), 3.72 (br. s., 1H), 3.85 (dd, J=12.5, 6.4 Hz, 1H), 5.02 (t, J=8.7 Hz, 1H), 5.29 (br. s., 1H), 7.42-7.48 (m, 1H), 7.54 (td, J=7.7, 1.3 Hz, 1H), 7.96 (s, 1H), 8.02 (dd, J=15.2, 7.6 Hz, 2H), 8.14 (s, 1H), 8.21 (d, J=2.3 Hz, 1H), 8.33 (d, J=2.3 Hz, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08178668B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-b4d725be7a3845bbb491f94a7bfe3438 |
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| Source note | uspto-grants-2012_05 |
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