Sodium hydride → tert-butyl 4-(5-{[(4-nitro-1-phenyl-1H-pyrazol-3-yl)amino]carbonyl}pyridin-2-yl)piperazine-1-carboxylate

HRID 913255Notes

Reaction equation

HRID 913255 reaction equation
[N+:1]([C:4]1[C:5]([NH2:15])=[N:6][N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1)([O-:3])=[O:2].[H-].[Na+].[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][N:32]=2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].F[P-](F)(F)(F)(F)F.N1(O[P+](C(C)C)(C(C)C)C(C)C)C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[N+](C1C=CNN=1)([O-])=O.[H-].[Na+]>CN(C=O)C>[N+:1]([C:4]1[C:5]([NH:15][C:35]([C:34]2[CH:38]=[CH:39][C:31]([N:28]3[CH2:29][CH2:30][N:25]([C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:24])[CH2:26][CH2:27]3)=[N:32][CH:33]=2)=[O:36])=[N:6][N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1)([O-:3])=[O:2]

Participants

8

Reactant 6

HCID 24758Sodium hydrideHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27718236-(4-((Tert-butoxy)carbonyl)piperazin-1-yl)pyridine-3-carboxylic acidHCID 230849134-nitro-1-phenyl-1H-Pyrazol-3-amineHCID 86626029(1H-1,2,3-benzotriazol-1-yloxy)(triisopropyl)phosphonium hexafluorophosphateHCID 178526746HCID 178526746, compound

Product 1

HCID 67408038tert-butyl 4-(5-{[(4-nitro-1-phenyl-1H-pyrazol-3-yl)amino]carbonyl}pyridin-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4-nitro-1-phenyl-1H-pyrazol-3-amine (0.05 g, 0.25 mmol) in DMF (0.75 mL) was treated with sodium hydride (6 mg (60% in mineral oil), 0.27 mmol). In a separate flask 6-[4-(tert-butoxycarbonyl)piperazin-1-yl]nicotinic acid (0.075 g, 0.25 mmol) in DMF (0.75 mL) was treated with (1H-1,2,3-benzotriazol-1-yloxy)(triisopropyl)phosphonium hexafluorophosphate (0.16 g, 0.37 mmol) and this was stirred at ambient temperature for 1 hour. The acid/BOP solution was then transferred to the nitropyrazole/sodium hydride solution and the resulting reaction mixture was stirred at ambient temperature for 16 hours. The reaction was loaded directly onto a silica cartridge and purified by flash chromatography (20-30% ethyl acetate/hexanes) to give tert-butyl 4-(5-{[(4-nitro-1-phenyl-1H-pyrazol-3-yl)amino]carbonyl}pyridin-2-yl)piperazine-1-carboxylate as a yellow oil. ESIMS calcd 494.2 (M++H), found 494.1 (M++H).

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred at ambient temperature for 16 hours
  3. custompurified by flash chromatography (20-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d02ac8488e854ea18b025f143c057ebb
Source dataset
uspto-grants-2011_09
Patent number
US08026260B2

Reaction notes

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