Water → HCID 71287882, compound

HRID 83526Notes

Reaction equation

HRID 83526 reaction equation
Cl.Cl.[NH2:3][C@H:4]([CH2:28][NH2:29])[C:5]([NH:7][C:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][CH2:20][CH3:21])[CH:14]=2)[N:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:9]=1)=[O:6].[C:30](N1C=CN=C1)(N1C=CN=C1)=[O:31].C(N(CC)CC)C.O>CN(C)C=O>[C:22]1([N:10]2[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][CH2:20][CH3:21])[CH:14]=3)=[CH:12][C:8]([NH:7][C:5]([C@H:4]3[CH2:28][NH:29][C:30](=[O:31])[NH:3]3)=[O:6])=[N:9]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 86680362HCID 86680362, compound

Product 1

HCID 71287882HCID 71287882, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-2,3-diamino-N-[1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-yl]-propionamide dihydrochloride (181 mg) in N,N-dimethylformamide (3 ml) were added 1,1′-carbonyldiimidazole (67 mg), and triethylamine (116 μl) at room temperature, and the mixture was stirred for 16 hours. To this reaction solution was added water, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=10/1) to give the titled compound (76 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe resulting organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-37fd2c7ca8dc467d91021a26c1525b99
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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