Water → phenyl [1-(2-hydroxyethyl)-5-(tritylamino)-1H-pyrazol-4-yl]carbamate

HRID 459632Notes

Reaction equation

HRID 459632 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][OH:9])[N:5]=[CH:4][C:3]=1[NH:10][C:11](=[O:19])[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.[C:27](Cl)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>CN(C)C=O>[OH:9][CH2:8][CH2:7][N:6]1[C:2]([NH:1][C:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[C:3]([NH:10][C:11](=[O:19])[O:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:4]=[N:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 86597885HCID 86597885, compound

Product 1

HCID 86597886phenyl [1-(2-hydroxyethyl)-5-(tritylamino)-1H-pyrazol-4-yl]carbamateYield 33.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of phenyl [5-amino-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]carbamate (5.45 g) in N,N-dimethylformamide (55 ml) were added triethylamine (8.69 ml) and trityl chloride (6.37 g), and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture and the whole mixture was extracted with ethyl acetate. The extract was washed with water and brine and dried over anhydrous magnesium sulfate. Concentration under reduced pressure gave a crude product, which was triturated with ethyl acetate-diisopropyl ether (1:2). The resulting solid was collected by filtration to give phenyl [1-(2-hydroxyethyl)-5-(tritylamino)-1H-pyrazol-4-yl]carbamate (3.5 g).

Workup

  1. extractionthe whole mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentration under reduced pressure
  5. customgave a crude product, which
  6. customwas triturated with ethyl acetate-diisopropyl ether (1:2)
  7. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-d0a9372a5c534de589c50a18c5c08046
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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