Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanesulfonamide | HCID 73702 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | 4-((1-Benzhydrylazetidin-3-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid | HCID 86703780 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | HCID 86703781 | HCID 86703781 | — |
Reaction Steps
A mixture of 4-((1-benzhydrylazetidin-3-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid (35.6 mg), ethanesulfonamide (22.5 mg), HBTU (41.9 mg), and DIPEA (0.073 mL) in DCE (0.83 mL) was heated at 35° C. for 16 hr then at 55° C. for 1 hr. More ethyanesulfonamide (9 mg) was added. Heating continued for 1 hr. Added with 1M NaH2PO4, the contents were extracted with DCM (2×). The combined extracts were dried (Na2SO4). The crude was purified with HPLC (23 mg). LCMS (Method D): RT=5.08 min, m/z: 523.2 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 11.78 (s, 1H), 7.49-7.36 (m, 4H), 7.28 (dd, J=8.3, 6.8 Hz, 4H), 7.22-7.09 (m, 3H), 6.95 (d, J=12.8 Hz, 1H), 4.49 (s, 1H), 4.21 (d, J=6.2 Hz, 2H), 3.47-3.36 (m, 2H), 3.02 (s, 2H), 2.93-2.81 (m, 1H), 2.10-1.99 (m, 1H), 1.22 (t, J=7.5 Hz, 3H), 0.95-0.82 (m, 2H), 0.71-0.61 (m, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08952169B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-2951f399415f4bba8f59f1bdb39b10da |
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| Source note | uspto-grants-2015_02 |
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