Dimethylformamide → HCID 53714442, compound

HRID 129830Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[NH:8][N:7]=1)=[O:5])[CH3:2].[CH3:17]N(C)C=O.[H-].[Na+].Cl.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31]Cl>O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH:31]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][N:25]=2)[CH3:17])[N:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred mixture of 5-(2-pyridinyl)pyrazole-3-carboxylic acid ethyl ester (4.34 g) and anhydrous dimethylformamide (40 ml) at room temperature, 1.92 g of 60% sodium hydride oil suspension were added. After the bubbling had stopped, 3.60 g of 2-picolyl chloride hydrochloride were added. The resulting mixture was stirred at 50° C. overnight, poured into 300 ml of water and extracted with ethyl acetate (2×300 ml). The organic solution was dried over sodium sulfate and rotavaped. The residue was chromatographed (silica gel, EtOAc)to afford 1.93 g of 1-(1-(2-pyridinyl)ethyl)-3-(2-pyridinyl)pyrazole-5-carboxylic acid ethyl ester, as a viscous oil. NMR: 1.31 (t, 3H), 4.29 (q, 2H), 6.00 (s, 2H, 1-pyrazolyl CH2), 7.59 (s, 1H, 4-pyrazolyl H), 6.85, 7.16, 7.32. 7.81, 7.99, 8.57, 8.65 (8 m, 8H, pyridinyl H's). The column also yielded 0.58 g of 1-(1-(2-pyridinyl)ethyl)-5-(2-pyridinyl)pyrazole-3-carboxylic acid ethyl ester, as a viscous oil. NMR: 1.42 (t, 3H), 4.45 (q, 2H), 6.20 (s, 2H, 1-pyrazolyl CH2), 7.26 (s, 1H, 4-pyrazolyl H), 6.74, 7.09, 7.19, 7.51, 7.61, 7.72, 8.49, 8.53 (8 m, 8H, pyridinyl H's).

Workup

extractionextracted with ethyl acetate (2×300 ml)
dry with materialThe organic solution was dried over sodium sulfate
customThe residue was chromatographed (silica gel, EtOAc)

Sources & evidence

ORD record: ord-1a21720bb6a845b69f6e51997886510b
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05470862

Reaction notes

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