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

HRID 913256Notes

Reaction equation

HRID 913256 reaction equation
[N+:1]([C:4]1[C:5]([NH:15][C:16]([C:18]2[CH:19]=[CH:20][C:21]([N:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]3)=[N:22][CH:23]=2)=[O:17])=[N:6][N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1)([O-])=O>CO.[Pt](=O)=O>[NH2:1][C:4]1[C:5]([NH:15][C:16]([C:18]2[CH:19]=[CH:20][C:21]([N:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]3)=[N:22][CH:23]=2)=[O:17])=[N:6][N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1

Participants

4

Reactant 1

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

Product 1

HCID 16739137tert-butyl 4-(5-{[(4-amino-1-phenyl-1H-pyrazol-3-yl)amino]carbonyl}pyridin-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-(5-{[(4-nitro-1-phenyl-1H-pyrazol-3-yl)amino]carbonyl}pyridin-2-yl)piperazine-1-carboxylate (50 mg, 0.1 mmol) in methanol (10 mL) was degassed with nitrogen and treated with catalytic platinum(IV) oxide (25 mg). The solution was then placed under a hydrogen atmosphere with stirring for 20 minutes. The reaction was degassed with nitrogen, filtered through celite and evaporated to dryness. Purification by flash chromatography (0-4% methanol/methylene chloride) gave tert-butyl 4-(5-{[(4-amino-1-phenyl-1H-pyrazol-3-yl)amino]carbonyl}pyridin-2-yl)piperazine-1-carboxylate as a light yellow solid. 1H NMR (CDCl3) δ 8.78 (d, J=2.35, 1H), 8.13 (dd, J=9.01, 2.64 Hz, 1H), 7.78 (s, 1H), 7.64 (d, J=8.8 Hz, 2H), 7.42, (t, J=7.33 Hz, 2H), 7.22 (t, J=7.34, 1H), 6.88 (d, J=9.09 Hz, 1H), 3.71 (t, J=5.28 Hz, 2H), 3.54 (bs, 2H), 1.48 (s, 9H); ESIMS calcd 464.2 (M++H), found 464.2 (M++H).

Workup

  1. customThe reaction was degassed with nitrogen
  2. filtrationfiltered through celite
  3. customevaporated to dryness
  4. customPurification by flash chromatography (0-4% methanol/methylene chloride)

Sources & evidence

ORD record
ord-51b9d143dfe84aba885a65b38e63e271
Source dataset
uspto-grants-2011_09
Patent number
US08026260B2

Reaction notes

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