Cyclopropanecarboximidamide hydrochloride → HCID 178490489, compound

HRID 2097976Notes

Reaction equation

[NH:1]([C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][C:11](=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)=O)[NH2:2].[CH2:22]1[CH:24]([C:25](N)=[NH:26])[CH2:23]1.Cl.C[O-].[Na+]>C(O)C.[Cl-].[Na+].O>[CH:24]1([C:25]2[N:26]=[C:3]([C:5]3[S:6][CH:7]=[CH:8][C:9]=3[NH:10][C:11](=[O:21])[CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[NH:1][N:2]=2)[CH2:22][CH2:23]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of N-(2-(hydrazinecarbonyl)thiophen-3-yl)-2-(4-methoxyphenyl)acetamide (101 mg, 0.30 mmol), cyclopropylcarbamidine hydrochloride (47 mg, 0.39 mmol) and sodium methoxide (39 mg, 0.72 mmol) in ethanol (3 mL) was stirred at 120° C. for 17 h. The mixture was diluted with brine and extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), filtered, concentrated under vacuum and purified by preparative HPLC to give N-(2-(3-cyclopropyl-1H-1,2,4-triazol-5-yl)thiophen-3-yl)-2-(4-methoxyphenyl)acetamide. Retention time (min)=5.578, method [7], MS (ESI) 354.43 (M+H); 1H NMR (300 MHz, CDCl3) δ 10.48 (s, 1H), 8.11 (d, J=5.6 Hz, 1H), 7.25-7.32 (m, 3H), 6.94 (d, J=8.8 Hz, 2H), 3.83 (s, 3H), 3.74 (s, 2H), 1.98-2.03 (m, 1H), 1.07-1.17 (m, 4H).

Workup

extractionextracted with ethyl acetate
customThe organic phase was separated
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated under vacuum
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-cf913879fb3e491086b03eb85840cab9
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450363B2

Reaction notes

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