4-Nitro-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehyde → HCID 178483736, compound

HRID 2274418Notes

Reaction equation

HRID 2274418 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][NH:5][C:6]1[CH:7]=[C:8]([NH2:14])[C:9]([NH2:13])=[CH:10][C:11]=1[F:12].[N+:16]([C:19]1[C:20]([CH:30]=O)=[N:21][N:22]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH:23]=1)([O-:18])=[O:17]>CO>[F:12][C:11]1[C:6]([NH:5][CH2:4][CH2:3][N:2]([CH3:15])[CH3:1])=[CH:7][C:8]2[NH:14][C:30]([C:20]3[C:19]([N+:16]([O-:18])=[O:17])=[CH:23][N:22]([CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][O:25]4)[N:21]=3)=[N:13][C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 224778374-Nitro-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehydeHCID 68842684HCID 68842684, compound

Product 1

HCID 178483736HCID 178483736, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1 g of N4-(2-dimethylaminoethyl)-5-fluorobenzene-1,2,4-triamine in 30 mL of methanol with 1.06 g of 4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazole-3-carbaldehyde is stirred at ambient temperature for 72 hours. After evaporation of the solvent under vacuum in a rotary evaporator, the reaction crude is purified by flash chromatography on an Intelliflash apparatus on an Analogix RS-90 cartridge with an eluent of 100% dichloromethane to 85/15 dichloromethane/methanol. 350 mg of N1-{6-fluoro-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-3H-benzimidazol-5-yl}-N2,N2-dimethylethane-1,2-diamine are isolated in the form of an orange foam. ES mass spectrum: 418(+)=(M+H)(+); 334(+)=(M+H)(+)-THP+H, 209.6=(M+2H)(2+)

Workup

  1. customAfter evaporation of the solvent under vacuum
  2. customin a rotary evaporator
  3. customthe reaction crude
  4. customis purified by flash chromatography on an Intelliflash apparatus on an Analogix RS-90 cartridge with an eluent of 100% dichloromethane to 85/15 dichloromethane/methanol

Sources & evidence

ORD record
ord-ac81d3ee403f4e348be5d677631989dc
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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