Pyrazole → N-(4-tert-butylphenyl)-6-(1H-pyrazol-1-yl)nicotinamide

HRID 736383Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[H-].[Na+].[C:8]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:27])[C:20]2[CH:25]=[CH:24][C:23](Cl)=[N:22][CH:21]=2)=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9]>CN(C=O)C>[C:8]([C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:27])[C:20]2[CH:25]=[CH:24][C:23]([N:1]3[CH:5]=[CH:4][CH:3]=[N:2]3)=[N:22][CH:21]=2)=[CH:16][CH:17]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

Conditions

Temperature: 100 °C

Procedure

Pyrazole (0.34 g, 5 mmol) in 10 mL of DMF was treated with sodium hydride (0.2 g in 60% mineral oil) at room temperature. The mixture was then treated with the product from Example 21A in DMF (20 mL) and heated at 100° C. for 4 hours. The reaction mixture was allowed to cool to room temperature and quenched with water. The mixture was filtered and the filter cake was collected as the title compound. 1H NMR (300 MHz, DMSO-d6) δ 10.39 (bs, 1H), 9.01 (dd, 1H), 8.71 (dd, 1H), 8.52 (dd, 1H), 8.07 (d, 1H), 7.7 (m, 1H), 7.65 (m, 2H), 7.4 (m, 2H), 6.6 (m, 1H) 1.25 (s, 9H); MS (ESI+) m/z 321 (M+H)+.

Workup

temperatureto cool to room temperature
customquenched with water
filtrationThe mixture was filtered
customthe filter cake was collected as the title compound

Sources & evidence

ORD record: ord-1f0613dee6c548afacc01352b2bcc0a9
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595332B2

Reaction notes

Loading…