Diisopropylethylamine → HCID 59408738, compound

HRID 1188098Notes

Reaction equation

HRID 1188098 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]([C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)=[CH:29][C:28]([C:38]([OH:40])=O)=[N:27]1.[I-].Cl[C:43]1C=CC=C[N+]=1C.CCN(C(C)C)C(C)C>C(Cl)Cl.O>[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[N:26]1[C:30]([C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)=[CH:29][C:28]([C:38]([NH:18][C:9]2[CH:8]=[C:7]([C:2]3[CH:1]=[CH:6][C:5]([CH3:43])=[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:40])=[N:27]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 59408776HCID 59408776, compoundHCID 68668178HCID 68668178, compound2×

Product 1

HCID 59408738HCID 59408738, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-Tolyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-amine (compound A, 81 mg, 0.31 mmol) was added to a solution of 1-(tetrahydro-2H-pyran-2-yl)-5-p-tolyl-1H-pyrazole-3-carboxylic acid (100 mg, 0.34 mmol), 2-chloro-1-methylpyridinium iodide (122 mg, 0.47 mmol) and N,N′-diisopropylethylamine (163 μL, 0.94 mmol) in DCM (10 mL). The reaction mixture was stirred at RT for 16 hrs. The reaction mixture was diluted with water and extracted with DCM. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by silica gel column chromatography (PE-EtOAc, 9:1) and gave 1-(tetrahydro-2H-pyran-2-yl)-N-(1-(tetrahydro-2H-pyran-2-yl)-5-p-tolyl-1H-pyrazol-3-yl)-5-p-tolyl-1H-pyrazole-3-carboxamide (70 mg, 43%).

Workup

  1. extractionextracted with DCM
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel column chromatography (PE-EtOAc, 9:1)

Sources & evidence

ORD record
ord-1a15024cc5f24e9a8d8e02d34d851f43
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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