HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1822927
Notes
Print preview

Reaction equation

HRID 1822927 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 4811429N-(4-tert-butylphenyl)-6-chloronicotinamide

Product 1

HCID 11186276N-(4-tert-butylphenyl)-6-(1H-pyrazol-1-yl)nicotinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

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

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

Sources & evidence

ORD record
ord-a14d253c1c62458c9dfc9f6c7787993d
Source dataset
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07037927B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes