Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Trimethylamine | HCID 1146 | — |
| Reactant | N1-(4-(2-(4-(((2-Chloroethyl)(methyl)amino)methyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-N3-phenylmalonamide | HCID 58790370 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 16041606 | HCID 16041606 | 22.7% |
Reaction Steps
To a solution of 88 (80 mg, 0.133 mmol) in DME (1 mL) was added NMe3 (15.7 mg, 2 eq, 0.27 mmol) and the reaction mixture was heated to 100° C. in a sealed tube for an hour. The mixture was cooled to RT and concentrated. Purification (Gilson, 45 mins, 40% MeOH in water to 80% MeOH in water) afforded title compound 84 (20 mg, 9% yield). 1H NMR (DMSO-d6) δ (ppm): 10.85 (s, 1H), 10.41 (s, 1H), 8.47 (m, 2H), 8.05 (s, 1H), 7.85 (m, 3H), 7.59 (m, 2H), 7.42 (m, 5H), 7.32 (m, 2H), 7.05 (t, J=7.43 Hz, 1H), 6.63 (d, J=5.67, 1H), 3.60 (s, 2H), 3.51 (m, 2H), 3.1 (s, 9H), 2.81 (m, 2H), 2.20 (s, 3H). MS (m/z) 626.1 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08093264B2 |
|---|
| Source dataset | uspto-grants-2012_01 |
|---|
| ORD ID | ord-45b6efcd64314d18a2f268eb59d7b00f |
|---|
| Source note | uspto-grants-2012_01 |
|---|
