Water → HCID 22273557, compound

HRID 2375279Notes

Reaction equation

CN(C)[CH:3]=[CH:4][C:5]([C:7]1[N:11]([CH2:12][CH3:13])[C:10]([CH3:14])=[N:9][CH:8]=1)=O.C(=O)(O)O.[C:20]1([NH:26][C:27]([NH2:29])=[NH:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C[O-].[Na+].O>CC(N(C)C)=O>[NH:26]([C:27]1[N:29]=[C:5]([C:7]2[N:11]([CH2:12][CH3:13])[C:10]([CH3:14])=[N:9][CH:8]=2)[CH:4]=[CH:3][N:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 110 °C

Procedure

5-(3-Dimethylaminoprop-2-en-1-oyl)-1-ethyl-2-methylimidazole (Method 23; 2.10 g, 10.1 mmol), phenylguanidine hydrogen carbonate (2.2 g, 11.1 mmol) and sodium methoxide (1.2 g, 22.2 mmol) were suspended in anhydrous DMA (15 ml) and the mixture heated at 110° C. for 18 hours. The reaction mixture was allowed to cool to ambient temperature and poured into water (50 ml). The solution was extracted EtOAc (2×50 ml). The combined extracts were washed with water (2×50 ml) and then brine (2×50 ml), dried and the volatiles removed by evaporation. The residue was triturated with ether, collected by filtration and air dried to give the title compound (1.48 g, 53%) as a reddish brown solid. NMR 1.17 (t, 3H), 2.38 (s, 3H), 4.52 (q, 2H), 6.93 (t, 1H), 7.08 (d, 1H), 7.27 (t, 2H), 7.60 (s, 1H),7.62 (d, 2H), 8.35 (d, 1H), 9.35 (s, 1H); m/z 280.

Workup

temperatureto cool to ambient temperature
extractionThe solution was extracted EtOAc (2×50 ml)
washThe combined extracts were washed with water (2×50 ml)
dry with materialbrine (2×50 ml), dried
customthe volatiles removed by evaporation
customThe residue was triturated with ether
filtrationcollected by filtration and air
customdried

Sources & evidence

ORD record: ord-a2c35f06cc414ffbafe1f6a2ca616a0c
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465728B2

Reaction notes

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