Trityl chloride → N-[2-(1-methyl-5-triphenylmethylaminopyrazol-4-yl)ethyl]formamide

HRID 349531Notes

Reaction equation

HRID 349531 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:10][CH:11]=[O:12].C(N(CC)CC)C.[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(Cl)Cl>[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]([CH2:8][CH2:9][NH:10][CH:11]=[O:12])[CH:4]=[N:5]1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 17962016N-[2-(5-amino-1-methylpyrazol-4-yl)ethyl]formamide

Product 1

HCID 17962019N-[2-(1-methyl-5-triphenylmethylaminopyrazol-4-yl)ethyl]formamideYield 71.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[2-(5-amino-1-methylpyrazol-4-yl)ethyl]formamide (2.7 g, 16 mmol) and triethylamine (2.5 ml, 17.6 mmol) in methylene chloride (50 ml) was added triphenylmethyl chloride (5.2 g, 17.6 mmol), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was washed with successively 10% aqueous citric acid solution and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with diisopropyl ether and dried in vacuo to give N-[2-(1-methyl-5-triphenylmethylaminopyrazol-4-yl)ethyl]formamide (4.7 g) as a colorless solid.

Workup

  1. washThe reaction mixture was washed with successively 10% aqueous citric acid solution and brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with diisopropyl ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-760693b07e06409fbc5286b0c00b03ac
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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