Trityl chloride → HCID 69463528, compound

HRID 1247781Notes

Reaction equation

HRID 1247781 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:19])[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].[C:20]1([C:26](Cl)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[CH3:7][N:6]1[C:2]([NH:1][C:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[C:3]([NH:8][C:9](=[O:19])[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH:4]=[N:5]1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 69464877HCID 69464877, compound

Product 1

HCID 69463528HCID 69463528, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 2-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-2-oxoethylcarbamate (307 g) in N,N-dimethylformamide (1.5 L) was added triphenylmethyl chloride (334 g). To the mixture was added triethylamine (318 ml) dropwise. The mixture was stirred at room temperature for 1 hour. The reaction mixture was dissolved in ethyl acetate. The solution was washed successively with water, 10% aqueous citric acid solution, water and brine. The extract was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was triturated with acetonitrile (1.5 L) and dried in vacuo to give tert-butyl 2-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-2-oxoethylcarbamate (468 g).

Workup

  1. washThe solution was washed successively with water, 10% aqueous citric acid solution, water and brine
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with acetonitrile (1.5 L)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-f93f868809e447e18b2c0fa12152ca80
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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