HCID 16780526, compound → HCID 16780512, compound

HRID 1063808Notes

Reaction equation

HRID 1063808 reaction equation
[CH2:1]([C:5]1[NH:9][N:8]=[C:7]([C:10]([NH2:12])=[O:11])[C:6]=1[N+:13]([O-])=O)[CH:2]([CH3:4])[CH3:3]>[Pd].C(O)C>[NH2:13][C:6]1[C:7]([C:10]([NH2:12])=[O:11])=[N:8][NH:9][C:5]=1[CH2:1][CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 16780526HCID 16780526, compound

Product 1

HCID 16780512HCID 16780512, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-Isobutyl-4-nitro-1H-pyrazol-3-carboxylic acid amide (4.7 g, 22 mmol) and 10% palladium on carbon (300 mg) in ethanol (80 ml) was stirred under hydrogen (60 psi) at room temperature for 4 hours, and held under nitrogen for 64 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure of dichloromethane:methanol (100:0 changing to 95:5 then 90:10, by volume) to give 4-amino-5-isobutyl-1H-pyrazol-3-carboxylic acid amide (3.8 g) as an off-white solid, which was a mixture of rotamers. 1H NMR (400 MHz, DMSO-D6): δ=12.20-12.28 (1H, brs), 7.00-7.10 (1.34H, brs), 6.80-6.85 (0.66H, brs), 4.27-4.40 (2H, brs), 2.27-2.36 (2H, d), 1.78-1.88 (1H, m), 0.77-0.84 (6H, d) ppm. LRMS (electrospray): m/z [M+H]+ 183, [M+Na]+ 205. Anal. Found C, 52.27; H, 7.78; N, 30.59. C8H14N4O requires C, 52.73; H, 7.76; N, 30.75%.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure of dichloromethane:methanol (100:0 changing to 95:5

Sources & evidence

ORD record
ord-6849c1cbce31407f9c25ea0cad9e924d
Source dataset
uspto-grants-2005_11
Patent number
US06967204B2

Reaction notes

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