Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Iodoethane | HCID 6340 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 49835078 | HCID 49835078 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 49835082 | HCID 49835082 | — |
Reaction Steps
A mixture of 8-(3,4-dimethoxy-phenyl)-1-(1,3-dimethyl-1H-pyrazol-4-yl)-1,3-dihydro-1,3,5,9-tetraaza-cyclopenta[a]naphthalen-2-one (Example 249, 50 mg, 0.120 mmol) and NaH 55% (8 mg, 0.183 mmol) in DMF was stirred at rt for 25 min. Then iodoethane (0.015 ml, 0.186 mmol) was added and the RM was stirred at rt for 5.5 h. After that, the RM was quenched with saturated aqueous NaHCO3, the suspension was then filtered, the cake was washed with water and dried in the vacuum oven to give the title compound as a white solid. (HPLC: tR 2.74 min (Method A); M+H=445 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 9.03 (s, 1H), 8.40-8.32 (m, 1H), 8.25-8.19 (m, 1H), 7.95 (s, 1H), 7.60-7.52 (m, 1H), 7.41-7.36 (m, 1H), 7.04-6.97 (m, 1H), 4.11 (q, 2H), 3.85 (s, 3H), 3.83 (s, 3H), 3.81 (s, 3H), 1.94 (s, 3H), 1.37 (t, 3H))
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08476294B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-c4b6282a5bbe433ea59bc76b13550b88 |
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| Source note | uspto-grants-2013_07 |
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