Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Bromoacetonitrile | HCID 11534 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 7-[(R)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-3-(1,2,3,6-tetrahydropyridin-4-yl)furo[3,2-c]pyridin-6-ylamine | HCID 57812480 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 57812759 | HCID 57812759 | — |
Reaction Steps
7-[(R)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-3-(1,2,3,6-tetrahydropyridin-4-yl)furo[3,2-c]pyridin-6-ylamine (10.0 mg, 0.0237 mmol), DIPEA (16.5 μL, 0.0947 mmol) and DMF (1.00 mL, 12.9 mmol) were mixed. Bromoacetonitrile (1.7 μL, 0.026 mmol) was added at last at 0° C. The mixture was stirred at 0° C. for 2 hours. Crude was passed through SCX-2 SPE, and the product was released by 2 M NH3 in methanol and purified on the MDPS. MS (ES+): m/z 461.03/463.05 (100/81) [MH+]. HPLC: tR=0.83 min (HPLC-ACQUITY, Analytical). 1H NMR (400 MHz, DMSO-d6): δ=1.82 (d, J=6.8 Hz, 3H), 2.46 (br. s., 2H), 2.65-2.74 (m, 2H), 3.19-3.22 (m, 2H), 3.85 (s, 2H), 5.60 (s, 2H), 6.21 (q, J=6.6 Hz, 1H), 6.31 (br. s., 1H), 7.45 (t, J=8.7 Hz, 1H), 7.52 (dd, J=9.0, 5.2 Hz, 1H), 7.78 (s, 1H), 8.30 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08022206B2 |
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| Source dataset | uspto-grants-2011_09 |
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| ORD ID | ord-ebcb8f2ead3948f986c9901c1ed9719d |
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| Source note | uspto-grants-2011_09 |
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