Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 3-(1-Oxido-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-yl)-1-propanol | HCID 11951644 | — |
| Reactant | 4-(Dimethylamino)butyric acid hydrochloride | HCID 12691640 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 57786563 | HCID 57786563 | 94% |
Reaction Steps
A mixture of alcohol 70 (100 mg, 0.41 mmol), 4-(dimethylamino)butanoic acid hydrochloride (68 mg, 0.41 mmol), DCC (93 mg, 0.45 mmol), DMAP (5 mg, 0.04 mmol) and Et3N (0.06 mL, 0.41 mmol) in DCM (20 mL) was stirred at 20° C. for 16 h. The solvent was evaporated and the residue purified by chromatography, eluting with a gradient (0-10%) of MeOH/20% EtOAc/DCM, to give the ester 309 (137 mg, 94%) as a pale-brown oil: 1H NMR δ 8.25 (s, 1H, H-9), 7.74 (s, 1H, H-5), 4.21 (t, J=6.3 Hz, 2H, CH2O), 3.06-3.15 (m, 6H, H-6, H-8, CH2), 2.73 (br s, 2H, H-7), 2.56 [s, 6H, N(CH3)2], 2.37 (t, J=7.0 Hz, 2H, CH2), 2.18-2.29 (m, 4H, CH2), 1.92-1.99 (m, 2H, CH2); 13C NMR δ 172.6, 164.9, 154.9, 149.1, 147.4, 132.3, 122.7, 114.2, 63.7, 57.7, 43.9 (2), 33.6, 33.2, 32.8, 31.3, 26.8, 25.7, 21.0; HRMS calcd for C19H26N4O3 (M+) m/z 358.2005, found 358.2006.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07989451B2 |
|---|
| Source dataset | uspto-grants-2011_08 |
|---|
| ORD ID | ord-06a97dc2b6ac42baada8ac8ac10457c6 |
|---|
| Source note | uspto-grants-2011_08 |
|---|
