Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | tert-butyl N-methyl-N-(2-oxoethyl)carbamate | HCID 10725881 | — |
| Reactant | (R)-N2-Indan-1-yl-quinoline-2,6-diamine | HCID 57860958 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 44218572 | HCID 44218572 | 77.3% |
Reaction Steps
A mixture of (R)—N2-indan-1-yl-quinoline-2,6-diamine (453 mg, 1.645 mmol) in Methanol (10 mL) with acetic acid (0.3 mL, 4.935 mmol) and commercially available methyl-(2-oxo-ethyl)carbamic acid tert-butyl ester (300 mg, 1.731 mmol) was stirred at 23° C. for 1 h. Portionwise addition of sodium cyanoborohydride (286 mg, 4.11 mmol) was followed by additional stirring at 23° C. for 3 h. Poured onto saturated NaHCO3-solution and extracted twice with ethyl acetate, dried over Na2SO4 and evaporated totally gave a crude product which was purified by flash chromatography with heptane and ethyl acetate to give the title compound as a yellow foam (550 mg, 73%); MS: m/e=433.4 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08183380B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-104bd243103540f4a60a03e7b419e161 |
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| Source note | uspto-grants-2012_05 |
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