Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethanamine, 2-fluoro-, hydrochloride | HCID 9995 | — |
| Reactant | Propylphosphonic anhydride | HCID 111923 | — |
| Reactant | HCID 117819062 | HCID 117819062 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 90466853 | HCID 90466853 | 44.3% |
Reaction Steps
See FIG. 21(a). 6-methyl-1-((3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (111 mg, 0.29 mmol) was taken dichloromethane (10 mL). Triethyl amine (0.204 mL, 1.46 mmol) was added to get a clear solution. 1-Propanephosphonic acid cyclic anhydride (0.348 mL, 0.59 mmol) was added and stirred at RT for 5 minutes. Added 2-Fluoroethylamine hydrochloride (87 mg, 0.88 mmol) and stirred at RT for overnight. After the completion of the reaction, diluted the reaction mass with dichloromethane, washed with water, brine solution. The organic layer was separated, dried over sodium sulphate, evaporated to get the crude compound. The compound was purified by silica gel chromatography using methanol and dichloromethane as eluent. Yield-44.3%. ES+MS m/z: 425.2 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.24 (s, 3 H ) 2.39 (s, 3 H ) 3.66 (q, J=5.21 Hz, 1 H ) 3.75 (q, J=5.15 Hz, 1 H ) 4.49 (t, J=4.99 Hz, 1 H ) 4.65 (t, J=4.99 Hz, 1 H ) 4.90 (q, J=8.85 Hz, 2 H ) 5.63 (s, 2 H ) 7.07 (d, J=5.65 Hz, 1 H ) 7.76 (s, 1 H ) 8.11 (s, 1 H ) 8.17 (d, J=5.65 Hz, 1 H ) 8.34 (s, 1 H ) 8.88 (t, J=5.84 Hz, 1 H ).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09163020B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-73b3338a9f2647b5ac2f520529a617ba |
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| Source note | uspto-grants-2015_10 |
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