Diisopropylethylamine → HCID 59408739, compound

HRID 1188144Notes

Reaction equation

HRID 1188144 reaction equation
[C:1]1(C)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[N:10]=[C:9]([NH2:18])[CH:8]=1.[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[N:26]1[C:30]([N+:31]([O-:33])=[O:32])=[CH:29][C:28]([C:34]([OH:36])=O)=[N:27]1.[I-].Cl[C:39]1C=CC=C[N+]=1C.CCN(C(C)C)C(C)C>C(Cl)Cl.O>[N+:31]([C:30]1[N:26]([CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25][O:20]2)[N:27]=[C:28]([C:34]([NH:18][C:9]2[CH:8]=[C:7]([C:2]3[CH:1]=[CH:6][C:5]([CH3:39])=[CH:4][CH:3]=3)[N:11]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[N:10]=2)=[O:36])[CH:29]=1)([O-:33])=[O:32]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 59408777HCID 59408777, compoundHCID 68668178HCID 68668178, compound

Product 1

HCID 59408739HCID 59408739, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-Tolyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-amine (97 mg, 0.38 mmol) was added to a solution of 1-(tetrahydro-2H-pyran-2-yl)-5-nitro-1H-pyrazole-3-carboxylic acid (100 mg, 0.41 mmol), 2-chloro-1-methylpyridinium iodide (145 mg, 0.56 mmol) and N,N′-diisopropylethylamine (193 L, 1.13 mmol) in DCM (10 mL). The reaction mixture was stirred at room temperature for 16 hrs. The reaction was diluted with water and extracted with DCM. The organic layer was washed with brine, dried with Na2SO4 and concentrated. The crude product was purified by silica gel column chromatography (PE-EtOAc, 8:2) and gave 5-nitro-1-(tetrahydro-2H-pyran-2-yl)-N-(1-(tetrahydro-2H-pyran-2-yl)-5-p-tolyl-1H-pyrazol-3-yl)-1H-pyrazole-3-carboxamide (60 mg, 33%).

Workup

  1. extractionextracted with DCM
  2. washThe organic layer was washed with brine
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel column chromatography (PE-EtOAc, 8:2)

Sources & evidence

ORD record
ord-6778ccad08dd4ff9a89a4574ab5644f5
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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