Sodium Methoxide → HCID 69314682, compound

HRID 2117755Notes

Reaction equation

CN(C)[CH:3]=[CH:4][C:5]([C:7]1[N:11]([CH:12]([CH3:14])[CH3:13])[C:10]([CH2:15][O:16][CH3:17])=[N:9][CH:8]=1)=O.C(=O)(O)O.[C:23]1([NH:29][C:30]([NH2:32])=[NH:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C[O-].[Na+]>CC(N(C)C)=O>[NH:29]([C:30]1[N:32]=[C:5]([C:7]2[N:11]([CH:12]([CH3:14])[CH3:13])[C:10]([CH2:15][O:16][CH3:17])=[N:9][CH:8]=2)[CH:4]=[CH:3][N:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 110 °C

Procedure

5-(3-Dimethylaminoprop-2-en-1-oyl)-1-isopropyl-2-methoxymethylimidazole (Method 50; 1.26 g, 5 mmol), phenylguanidine hydrogen carbonate (1.09 g, 5.5 mmol) and sodium methoxide (594 mg, 11 mmol) were suspended in anhydrous DMA (10 ml) and the mixture heated at 110° C. for 3 hours. The volatiles were evaporated in vacuo the residues was suspended in water (50 ml). The solution was extracted DCM (3×50 ml). The combined extracts were washed with water (50 ml) and then brine (50 ml), dried and the volatiles removed by evaporation. The residue was purified by flash silica chromatography eluting with DCM:MeOH (100:0 increasing in polarity to 97:3) to give the title compound as brown oil. NMR: 1.43 (d, 6H), 3.30 (s, 3H), 4.56 (s, 2H), 5.54 (m, 1H), 6.96 (t, 1H), 7.05 (d, 1H), 7.24 (t,2H), 7.44 (s, 1H), 7.65 (d, 2H), 8.41 (d, 1H), 9.42 (s, 1H); m/z 324.

Workup

customThe volatiles were evaporated in vacuo the residues
extractionThe solution was extracted DCM (3×50 ml)
washThe combined extracts were washed with water (50 ml)
dry with materialbrine (50 ml), dried
customthe volatiles removed by evaporation
customThe residue was purified by flash silica chromatography
washeluting with DCM:MeOH (100:0 increasing in polarity to 97:3)

Sources & evidence

ORD record: ord-c326c4f707b84ec5b304512f74f99986
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442697B2

Reaction notes

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