Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester | HCID 613145 | — |
| Reactant | HCID 24753671 | HCID 24753671 | — |
| Product | HCID 57611885 | HCID 57611885 | — |
Reaction Steps
N-[2-amino-5-(2-thienyl)phenyl]-4-(1,2-diamino-2-oxoethyl)benzamide (51 mg, 0.086 mmol) and DIPEA (52.4 μL, 0.300 mmol) were suspended in THF (1 mL) and acetic anyhdride (13 μL, 0.138 mmol) was added. The mixture was stirred at room temperature overnight. 2N HCl was added and the products extracted into EtOAc. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by prep-HPLC to give the desired product as a blue-green solid. 1H NMR (DMSO-d6, 600 MHz) δ 9.89 (s, 1H), 9.71 (s, 1H), 8.55 (d, J=7.8 Hz, 1H), 7.91 (m, 3H), 7.75 (s, 1H), 7.55 (m, 3H), 7.51 (d, J=5.4 Hz, 1H), 7.49 (m, 1H), 7.44 (m, 1H), 7.19 (s, 1H), 7.11 (m, 1H), 5.48 (d, J=7.8 Hz, 1H), 2.07 (s, 3H), 1.89 (s, 3H). MS: cal'd 451 (MH+), exp 451 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08168658B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-22af15d21ec34624a9428894737e86ac |
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| Source note | uspto-grants-2012_05 |
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