Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetohydrazide | HCID 14039 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733286 | — |
| Reactant | HCID 56597371 | HCID 56597371 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66653586 | HCID 66653586 | 42.9% |
Reaction Steps
29.6 mg (0.4 mmol) of acetohydrazide, 98.4 mg (0.3 mmol) of TOTU and 0.104 ml (0.6 mmol) of N,N-diisopropylethylamine are added, under an inert atmosphere, at 0° C., to 93.7 mg (0.2 mmol) of 3-{3-[(2,4-dioxo-3-propyl-1,2,3,4-tetrahydroquinazolin-6-yl)carbonyl]imidazo[1,5-a]pyridin-1-yl}benzoic acid in 6 ml of DMF. The reaction medium is stirred for 1 hour at 0° C. and then for 6 hours at 50° C. and then concentrated under reduced pressure. The residue is taken up in 10 ml of methanol. The precipitate obtained is filtered off, washed with dyethyl ether and with pentane, and then dried under reduced pressure at 40° C. overnight. 45 mg of a yellow solid are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08759344B2 |
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| Source dataset | uspto-grants-2014_06 |
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| ORD ID | ord-86564e83b7f44601926a897d6e7750f3 |
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| Source note | uspto-grants-2014_06 |
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