Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 2-(4,5-Dichloro-2-nitrophenyl)acetic acid | HCID 244198 | — |
| Reactant | Ether hydrochloride | HCID 10953452 | — |
| Reactant | 2-(2-Nitro-4,5-dichlorophenyl)-N-methyl-N-[(+/-)-trans-2-(1-pyrrolidinyl)-7-nitro-1,2,3,4-tetrahydronaphth-1-yl]acetamide | HCID 22879436 | — |
| Product | Hydrochloric Acid | HCID 313 | — |
| Product | 2-(2-Nitro-4,5-dichlorophenyl)-N-methyl-N-[(1S)-1-(3-nitrophenyl)-2-(1-pyrrolidinyl)ethyl]acetamide | HCID 11420249 | — |
Reaction Steps
This compound was prepared via the general DCC/pyr coupling procedure from 8 (0.3690 g, 1.4801 mmol), 2-nitro-4,5-dichlorophenylacetic acid (0.7301 g, 2.920 mmol), DCC(0.6213 g, 3.01 mmol), and pyridine (0.24 mL, 3.01 mmol). The crude product was converted to the HCl salt with Et2O—HCl without chromatography and crystallized from MeOH to yield 13 HCl.(0.3232 g, 42%): m.p. (HCl salt) 165° C. (dec); 1H NMR (HCl salt, DMSO-d6) δ2.0 (br s, 4H, —CH2CH2—), 2.93 (s, 3H, —NCH3), 3.1-4.3 (complex, 6H, 3 —CH2—), 4.4 (s, 2H, benzylic methylene), 6.2 (m, 1H, —CH—), 7.7-7.8 (m, 2H, aromatic), 7.9 (s, 1H, aromatic), 8.14 (s, 1H, aromatic), 8.27 (d, J=7.7 Hz, 1H, aromatic), 8.43 (s, 1H, aromatic). MS(FAB) m/z 481. Anal. (C, H, N) C21H22N4O5Cl2 .HCl.0.5MeOH.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06750216B2 |
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| Source dataset | uspto-grants-2004_06 |
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| ORD ID | ord-87ce638e030a4c80b85ed3c789f67959 |
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| Source note | uspto-grants-2004_06 |
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