Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | HCID 86689870 | HCID 86689870 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 89650393 | HCID 89650393 | 137.4% |
Reaction Steps
To (R)—N—((S)-1-(3-chloro-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-2-methylpropane-2-sulfinamide (1.08 g, 3.23 mmol) in anhydrous MeOH (10 mL) was added HCl (4.0 mol/L) in dioxane (14 mL). The reaction mixture was stirred at 40° C. under N2 for 16 h. Volatile solvent was removed under reduced pressure. The crude product was triturated with DCM until solid is seen. Light yellow solid was filtered and dried under a high vacuum to afford 868.2 mg (89.3%) of (5)-1-(3-chloro-1H-pyrrolo-[3,2-b]pyridin-5-yl)ethanamine as HCl salt. 1H NMR (400 MHz, DMSO) δ 11.90 (br s, 1H), 8.47 (br s, 3H), 7.93 (d, J=8.5 Hz, 1H), 7.90 (d, J=2.9 Hz, 1H), 7.37 (d, J=8.5 Hz, 1H), 4.60 (dt, J=12.4, 6.1 Hz, 1H), 1.56 (d, J=6.8 Hz, 3H); MS (ESI) m/z: 196 [M+1]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08815877B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-e5959e7760f54ea38531dacc780578a3 |
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| Source note | uspto-grants-2014_08 |
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