Cyclohexylamine → HCID 22567295, compound

HRID 25395

Reaction equation

HRID 25395 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]([OH:15])=O)([O-:3])=[O:2].O[N:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C1(N)CCCCC1>O.ClCCl.C(N(CC)CC)C.CN(C)C=O>[CH:21]1([NH:17][C:13]([C:7]2[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[NH:9][N:8]=2)=[O:15])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:20]1

Participants

9

Reactant 4

HCID 7965CyclohexylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71446525-nitro-1H-indazole-3-carboxylic Acid

Product 1

HCID 22567295HCID 22567295, compoundYield 459.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

N-Cyclohexyl-5-nitro-1H-indazole-3-carboxamide can be obtained in the following way: a solution of 2.5 g of 5-nitro-1H-indazole-3-carboxylic acid, of 150 ml of dichloromethane, of 75 ml of dimethylformamide, 0.16 g of 1-hydroxybenzotriazole and of 2.75 g 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride is stirred for 15 minutes at a temperature of 25° C. 1.7 ml of cyclohexylamine and 1.7 ml of triethylamine are then added. The reaction medium is maintained with stirring for 70 hours and concentrated by evaporation under reduced pressure. The residue thus obtained is taken up with 50 ml of dichloromethane and 50 ml of diisopropyl ethyl. After filtration, the paste obtained is taken up with 80 ml of distilled water and the solid form is filtered through a sintered glass funnel, washed with two times 50 ml of water and then dried under reduced pressure. The resulting solid is taken up with 50 ml of ethyl acetate, filtered through a sintered glass filter, washed with two times 25 ml of ethyl acetate and dried at 50° C. under reduced pressure. 1.57 g of N-cyclohexyl-5-nitro-1H-indazole-3-carboxamide are thus obtained in the form of a beige solid (Rf=0.90, silica gel thin layer chromatography, eluent: chloroform/methanol/20% aqueous ammonia (12/3/0.5 by volume)).

Workup

  1. temperatureThe reaction medium is maintained
  2. concentrationconcentrated by evaporation under reduced pressure
  3. customThe residue thus obtained
  4. filtrationAfter filtration
  5. customthe paste obtained
  6. filtrationthe solid form is filtered through a sintered glass funnel
  7. washwashed with two times 50 ml of water
  8. customdried under reduced pressure
  9. filtrationfiltered through a sintered glass
  10. filtrationfilter
  11. washwashed with two times 25 ml of ethyl acetate
  12. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-712968c199714d1c9b6993c7f837df5b
Source dataset
uspto-grants-2005_02
Patent number
US06858638B2

Linked notes

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