Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sarcosine | HCID 1088 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | HCID 86661517 | HCID 86661517 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 46941016 | HCID 46941016 | — |
Reaction Steps
Sodium cyanoborohydride (35 mg, 0.55 mmol) was added into a solution of 4-(5-(2-(methoxymethyl)-2′-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)-2-methylbenzaldehyde (194 mg, 0.49 mmol) and 2-(methylamino)acetic acid (86 mg, 0.97 mmol) in a mixture of methanol (3 mL), DCM (3 mL) and acetic acid (75 μl). The mixture was stirred at room temperature overnight and the solvent was then removed in vacuo. The residue was purified by preparative HPLC to give the title compound as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 8.47-8.31 (1H, m), 8.15-8.09 (1H, m), 8.06-7.99 (2H, m), 7.69 (1H, d, J=7.9 Hz), 7.33-7.20 (4H, m), 7.11 (1H, d, J=7.4 Hz), 4.33 (2H, s), 4.21 (2H, m), 3.67 (2H, s), 3.30 (3H, s), 2.78 (3H, s), 2.54 (3H, s), 2.07 (3H, s). LC/MS (Method A): 472 (M+H)+. HPLC (Method F) Rt 3.19 min (Purity: 98.5%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08815919B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-00b2d4c676804924afa21b02fa6b13ef |
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| Source note | uspto-grants-2014_08 |
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