Hydrochloric Acid → HCID 178480794, compound

HRID 577700Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([NH2:10])=[NH:9])[CH:4]=[N:3]1.[C:11]([CH:13]([CH2:19][CH:20](OCC)OCC)[C:14](OCC)=[O:15])#[N:12].CO[Na].CO.Cl.[OH-].[Na+]>CCO.CO>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:10]=[C:14]([OH:15])[C:13]3[CH:19]=[CH:20][NH:12][C:11]=3[N:9]=2)[CH:4]=[N:3]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of crude 1-(1-methyl-1H-pyrazol-4-yl)guanidine (17.5 g, crude) and ethyl 2-cyano-4,4-diethoxybutanoate (13.08 g, 0.06 mol) in EtOH (50 mL) was added CH3ONa/CH3OH (150 mL, 0.06 mol) at 20° C., and the reaction mixture was stirred at 100° C. for 20 hrs. The pH was adjusted to 2 by HCl (6 M) and stirred for 30 min. Then pH was adjusted to 7-8 by aqueous NaOH (1 M). The reaction mixture was filtered and the filter cake was dried in vacuo to afford a first batch of pure product. The filtrate was concentrated in vacuo and the residue was purified by column chromatography eluted with CH2Cl2:MeOH=13:1 to afford the title compound (combined batches yielded 5 g, 43.5% yield over two steps). 1H NMR: (400 MHz, DMSO) δ ppm 11.21 (s, 1H), 10.28 (s, 1H), 8.44 (s, 1H), 7.88 (s, 1H), 7.50 (s, 1H), 6.67-6.68 (m, 1H), 6.22-6.24 (m, 1H), 3.79 (s, 3H).

Workup

stirringstirred for 30 min
filtrationThe reaction mixture was filtered
customthe filter cake was dried in vacuo
customto afford a first batch of pure product
concentrationThe filtrate was concentrated in vacuo
customthe residue was purified by column chromatography
washeluted with CH2Cl2

Sources & evidence

ORD record: ord-4e7e1aa9ed3649d0877c66400808b71c
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040547B2

Reaction notes

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