HCID 18420210, compound → HCID 23402486, compound

HRID 1063803Notes

Reaction equation

HRID 1063803 reaction equation
[C:1]([C:5]1[NH:9][N:8]=[C:7]([C:10]([NH2:12])=[O:11])[C:6]=1[N+:13]([O-])=O)([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[NH2:13][C:6]1[C:7]([C:10]([NH2:12])=[O:11])=[N:8][NH:9][C:5]=1[C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 18420210HCID 18420210, compound

Product 1

HCID 23402486HCID 23402486, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-tert-Butyl-4-nitro-1H-pyrazol-3-carboxylic acid amide (4.6 g, 21 mmol) and 10% palladium on carbon (300 mg) in ethanol (80 ml) was stirred under hydrogen (60 psi) at room temperature for 18 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was pre-absorbed onto silica gel and purified by flash column chromatography eluting with a solvent gradient of dichloromethane: methanol (100:0 changing to 95:5 then 90:10, by volume) to give 4-amino-5-tert-butyl-1H-pyrazol-3-carboxylic acid amide (2.96 g) as an off-white solid, which was a mixture of rotamers. 1H NMR (400 MHz, DMSO-D6): δ=12.10-12.20 (0.75H, brs), 11.75-11.85 (0.25H, brs), 7.04-7.16 (1.5H, brs), 6.88-6.96 (0.5H, brs), 4.27-4.59 (2H, 2×brs), 1.12 (9H, s) ppm. LRMS (electrospray): m/z [M+H]+ 183, [M+Na]+ 205, [M−H]+ 181. Anal. Found C, 52.45; H, 7.84; N, 30.62. C8H14N4O requires C, 52.73; H, 7.74; N, 30.75%.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was pre-absorbed onto silica gel
  4. custompurified by flash column chromatography
  5. washeluting with a solvent gradient of dichloromethane: methanol (100:0 changing to 95:5

Sources & evidence

ORD record
ord-da6f142c9e92499186e7684d0e45987a
Source dataset
uspto-grants-2005_11
Patent number
US06967204B2

Reaction notes

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