HCID 13883775, compound → 5-(3-Amino-1H-pyrazol-1-yl)pentanamide

HRID 543762Notes

Reaction equation

HRID 543762 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([NH2:15])=[O:14])[N:5]=1)([O-])=O>[Pd].C(O)(C)C>[NH2:1][C:4]1[CH:8]=[CH:7][N:6]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([NH2:15])=[O:14])[N:5]=1

Participants

4

Reactant 1

HCID 13883775HCID 13883775, compound

Product 1

HCID 202027755-(3-Amino-1H-pyrazol-1-yl)pentanamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 5-(3-nitropyrazol-1-yl)valeramide (3.6 g.) and 3% w/w palladium on carbon (0.54 g.) was stirred in isopropanol (20 ml.) under an atmosphere of hydrogen. The temperature was kept below 40° by external ice cooling. After 4 hours no more hydrogen was absorbed. The mixture was filtered and the filtrate was evaporated in vacuo to give 5-(3-aminopyrazol-1-yl)valeramide as an oil which crystallised. This product (2.5 g.) was stirred in acetonitrile (25 ml.) and 2,2,2-trifluoroethylisothiocyanate (2.17 g.) was added. After 18 hours the mixture was filtered and the residue was washed with acetonitrile then ether to give 5-(3-[3-(2,2,2-trifluoroethyl)thioureido]pyrazol-1-yl)valeramide, m.p. 172°-174°.

Workup

  1. customwas kept below 40° by external ice cooling
  2. customAfter 4 hours no more hydrogen was absorbed
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-51a57cb580d94f289069fd9c043893f3
Source dataset
uspto-grants-1984_05
Patent number
US04447441

Reaction notes

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