Cyclopropanecarboximidamide hydrochloride → HCID 178490489, compound

HRID 1519763Notes

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-b8983f0bcb5b48e6a2131a1196327263
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073891B2

Reaction notes

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