Trityl chloride → N-[3-(1-methyl-5-triphenylmethylaminopyrazol-4-yl)propyl]formamide

HRID 349525Notes

Reaction equation

HRID 349525 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][NH:11][CH:12]=[O:13].C(N(CC)CC)C.[C:21]1([C:27](Cl)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[CH3:7][N:6]1[C:2]([NH:1][C:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[C:3]([CH2:8][CH2:9][CH2:10][NH:11][CH:12]=[O:13])[CH:4]=[N:5]1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 17962035N-[3-(5-amino-1-methylpyrazol-4-yl)propyl]formamide

Product 1

HCID 17961975N-[3-(1-methyl-5-triphenylmethylaminopyrazol-4-yl)propyl]formamideYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[3-(5-amino-1-methylpyrazol-4-yl)propyl]formamide (3.64 g, 20 mmol) and triethylamine (2.23 g, 22 mmol) in methylene chloride (50 ml) was added triphenylmethyl chloride (6.13 g, 22 mmol). The mixture was stirred at room temperature for 90 minutes. The reaction mixture was washed with successively 10% aqueous citric acid solution, brine, and 10% aqueous sodium carbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with ethyl acetate and dried in vacuo to give N-[3-(1-methyl-5-triphenylmethylaminopyrazol-4-yl)propyl]formamide (6.8 g) as a solid.

Workup

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

Sources & evidence

ORD record
ord-3c23117367b8457db8ab6f5d274e3c99
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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