Trityl chloride → ethyl 3-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3-oxopropanoate

HRID 1247834Notes

Reaction equation

HRID 1247834 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].[C:17](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>CN(C)C=O>[CH3:7][N:6]1[C:2]([NH:1][C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:3]([NH:8][C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:4]=[N:5]1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 21904570Ethyl 3-((5-amino-1-methyl-1H-pyrazol-4-yl)amino)-3-oxopropanoate

Product 1

HCID 21904531ethyl 3-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3-oxopropanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The crude residue containing ethyl 3-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-3-oxopropanoate was dissolved in N,N-dimethylformamide (20 ml), and trityl chloride (5.52 g) and triethylamine (4.14 ml) were added with stirring. The mixture was stirred overnight and quenched with water (10 ml). The whole mixture was extracted with ethyl acetate, and the extract was washed with water and brine, dried over magnesium sulfate and concentrated under reduced pressure to give a residual oil, which was chromatographed on silica gel eluting with dichloromethane-ethyl acetate (2:3) to give ethyl 3-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3-oxopropanoate (1.23 g).

Workup

  1. stirringThe mixture was stirred overnight
  2. customquenched with water (10 ml)
  3. extractionThe whole mixture was extracted with ethyl acetate
  4. washthe extract was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a residual oil, which
  8. customwas chromatographed on silica gel eluting with dichloromethane-ethyl acetate (2:3)

Sources & evidence

ORD record
ord-4e67ed1b464f423692b74bf1274e03ab
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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