Ethanol → HCID 178435252, compound

HRID 2213282Notes

Reaction equation

CN(C)[CH:3]1[C:14]2[C:6](=[CH:7][CH:8]=[C:9]3[C:13]=2[S:12](=C)[CH:11]=[N:10]3)[NH:5][C:4]1=[O:16].[CH3:18][CH2:19][C:20]1([C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=2)[C:26](=[O:27])[NH:25][C:23](=[O:24])[CH2:22][CH2:21]1.[CH2:35](O)C>C(OCC)C>[CH2:19]([C:20]1([C:28]2[CH:29]=[CH:30][C:31]([NH:34]/[CH:35]=[C:3]3\[C:4](=[O:16])[NH:5][C:6]4[C:14]\3=[C:13]3[S:12][CH:11]=[N:10][C:9]3=[CH:8][CH:7]=4)=[CH:32][CH:33]=2)[CH2:21][CH2:22][C:23](=[O:24])[NH:25][C:26]1=[O:27])[CH3:18]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 8-dimethylamino-methylene-6,8-dihydro-1-thia-3,6-diaza-as-indacen-7-one (Procecure E, 0.040 g, 0.163 mmol), DL-aminoglutethimide (0.055 g, 0.237 mmol) in absolute ethanol (5 ml) was heated with stirring at 90° C. for 16 h. The reaction was diluted with ethanol and diethyl ether and the product collected by filtration to yield 0.038 g (54%) of the title compound. 1H NMR (DMSO-d6): δ 11.00 (d, 1H, J=12.5 Hz), 10.88 (s, 1H), 10.83 (s, 1H), 9.23 (s, H), 8.02 (d, 1H, J=12.5 Hz), 7.77 (d, 1H, J=8.6 Hz), 7.42 (d, 2H, J=8.9 Hz), 7.31 (d, 2H, J=8.9 Hz), 7.09 (d, 1H, J=8.2 Hz), 2.44–2.34 (m, 2H), 2.15–2.13 (m, 2H), 1.86–1.02 (m, 2H), 0.75 (t, 3H, J=7.3 Hz); ES-MS m/z 431 (M−H).

Workup

temperaturewas heated
filtrationthe product collected by filtration

Sources & evidence

ORD record: ord-3cf5edf33fb34cda9432499ac498139e
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105529B2

Reaction notes

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