HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-(2-Fluoro-4-(3-(2-(4-fluorophenyl)acetyl)ureido)phenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl ethylcarbamate → 1-(4-(6-(3-(Dimethylamino)propoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)urea, hydrochloride salt
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-(2-Fluoro-4-(3-(2-(4-fluorophenyl)acetyl)ureido)phenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl ethylcarbamate | HCID 11497346 | — |
| Reactant | 4-(6-(3-(Dimethylamino)propoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)-3-fluorobenzenamine | HCID 21081671 | — |
| Reactant | 1-(3-Fluoro-4-(5-methyl-6-(2-(4-methylpiperazin-1-yl)ethoxy)pyrrolo[2,1-f][1,2,4] triazin-4-yloxy)phenyl)-3-(2-(4-fluorophenyl)acetyl)thiourea, bis-hydrochloride salt | HCID 131726236 | — |
| Product | 1-(4-(6-(3-(Dimethylamino)propoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)urea, hydrochloride salt | HCID 131726237 | 13% |
Reaction Steps
4-(6-(3-(Dimethylamino)propoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)-3-fluorobenzenamine (12 mg, 0.03 mmol) was converted to the title compound (2.5 mg, 13%) in a manner similar to the preparation of Compound E of Example 31, except that 2-(4-fluorophenyl)-acetyl isocyanate (0.10 mL, 0.04 mmol, Compound C of Example 4) was used instead of benzenesulfonyl isocyanate. 1H NMR (CD3OD) δ 10.77 (s, 1H), 7.80 (s, 1H), 7.69 (s, 1H), 7.40-7.23 (m, 5H), 7.11-7.02 (m, 3H), 4.15-4.12 (m, 2H), 3.71 (s, 2H), 3.41-3.36 (m, 2H), 2.97 (s, 6H), 2.44 (s, 3H), 2.31-2.22 (m, 2H); HRMS(ESI), 539.2218 (M+H)+ calc, 539.2218 (M+H)+ found.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07439246B2 |
| Source dataset | uspto-grants-2008_10 |
| ORD ID | ord-d80d31b3eb0d4db6bc127524734333b3 |
| Source note | uspto-grants-2008_10 |