Diisopropylethylamine → HCID 59408779, compound

HRID 1188146Notes

Reaction equation

HRID 1188146 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)[N:5]=[C:4]([C:13]([NH:15][C:16]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)[N:18]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)[N:17]=2)=[O:14])[CH:3]=1.[O:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]1[N:40]1[C:44]([C:45]2[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][CH:46]=2)=[CH:43][C:42]([C:52](O)=[O:53])=[N:41]1.[I-].ClC1C=CC=C[N+]=1C.CCN(C(C)C)C(C)C>C(Cl)Cl.O>[O:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]1[N:40]1[C:44]([C:45]2[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][CH:46]=2)=[CH:43][C:42]([C:52]([NH:1][C:2]2[N:6]([CH:7]3[CH2:12][CH2:11][CH2:10][CH2:9][O:8]3)[N:5]=[C:4]([C:13](=[O:14])[NH:15][C:16]3[CH:20]=[C:19]([C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=4)[N:18]([CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][O:29]4)[N:17]=3)[CH:3]=2)=[O:53])=[N:41]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 59408756HCID 59408756, compoundHCID 59408776HCID 59408776, compound

Product 1

HCID 59408779HCID 59408779, compoundYield 17.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-Amino-1-(tetrahydro-2H-pyran-2-yl)-N-(1-(tetrahydro-2H-pyran-2-yl)-5-p-tolyl-1H-pyrazol-3-yl)-1H-pyrazole-3-carboxamide (102 mg, 0.23 mmol) was added to a solution of 1-(tetrahydro-2H-pyran-2-yl)-5-p-tolyl-1H-pyrazole-3-carboxylic acid (59 mg, 0.20 mmol), 2-chloro-1-methylpyridinium iodide (79 mg, 0.31 mmol) and N,N′-diisopropylethylamine (105 μL, 0.62 mmol) in DCM (10 mL). The reaction mixture was stirred at room temperature for 16 hrs. The reaction mixture 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, 7:3) and gave 1-(tetrahydro-2H-pyran-2-yl)-N-(1-(tetrahydro-2H-pyran-2-yl)-3-(1-(tetrahydro-2H-pyran-2-yl)-5-p-tolyl-1H-pyrazol-3-ylcarbamoyl)-1H-pyrazol-5-yl)-5-p-tolyl-1H-pyrazole-3-carboxamide (25 mg, 15%).

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, 7:3)

Sources & evidence

ORD record
ord-264d305f8e364c4ebeb25c968a53e46c
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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