HuagongsheHuagongshe Chemistry Print Report · For research reference only
Oxalyl chloride → 2-Chloro-5-(pivalamidomethyl)-N-(4-(3-(trifluoromethyl)phenoxy)quinazolin-8-yl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acid | HCID 58483208 | — |
| Reactant | 4-(3-(Trifluoromethyl)phenoxy)quinazolin-8-amine | HCID 71680391 | — |
| Catalyst | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-Chloro-5-(pivalamidomethyl)-N-(4-(3-(trifluoromethyl)phenoxy)quinazolin-8-yl)benzamide | HCID 71678715 | 32.8% |
Reaction Steps
The title compound was prepared following the procedure described in Example-1 using 4-(3-(trifluoromethyl)phenoxy)quinazolin-8-amine (Intermediate-8, 50 mg, 0.164 mmol), 2-chloro-5-(pivalamidomethyl)benzoic acid (Intermediate-5, 88 mg, 0.326 mmol), oxalyl chloride (59 mg, 0.47 mmol), DMF (1 drop) and DIPEA (63 mg, 0.49 mmol) in CH2Cl2 (2 mL) to afford 30 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.35 (s, 1H), 8.92 (d, 1H), 8.77 (s, 1H), 8.13 (d, J=7.8 Hz, 1H), 7.85 (m, 2H), 7.73 (s, 3H), 7.59-7.53 (m, 2H), 7.39 (d, J=7.2 Hz, 1H), 4.29 (d, J=5.4 Hz, 2H), 1.11 (s, 9H); MS [M+H]+: 557.14.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09006257B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-f32df9fed12a4a28b7d7ad6f43a3570e |
| Source note | uspto-grants-2015_04 |