Trityl chloride → 7-(3-{2-[(Tert-butoxycarbonyl)amino]ethyl)ureido)-2,3-dihydro-1-tritylimidazo[1,2-b]pyrazole

HRID 1247795Notes

Reaction equation

HRID 1247795 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].C(N(C(C)C)C(C)C)C.S(=O)(=O)(O)O.[NH2:38][C:39]1[CH:43]=[N:42][N:41]2[CH2:44][CH2:45][NH:46][C:40]=12.[C:47](Cl)([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C(Cl)Cl.C(N(CC)CC)C>[C:19]([O:18][C:17]([NH:16][CH2:15][CH2:14][NH:13][C:1](=[O:2])[NH:38][C:39]1[CH:43]=[N:42][N:41]2[CH2:44][CH2:45][N:46]([C:47]([C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C:40]=12)=[O:23])([CH3:20])([CH3:22])[CH3:21]

Participants

8

Reactant 5

HCID 6456Trityl chlorideHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 1358007252,3-dihydro-1H-imidazo[1,2-b]pyrazol-7-amine sulfate

Product 1

HCID 219044667-(3-{2-[(Tert-butoxycarbonyl)amino]ethyl)ureido)-2,3-dihydro-1-tritylimidazo[1,2-b]pyrazoleYield 14.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of 1,1′-carbonyldiimidazole (1.95 g) in methylene chloride (20 ml) was added tert-butyl N-(2-aminoethyl)carbamate (1.92 g) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. To the reaction mixture were added N-ethyldiisopropylamine (2.59 g) and 7-amino-2,3-dihydro-1H-imidazo[1,2-b]pyrazole sulfuric acid salt (2.22 g), and the mixture was stirred at room temperature for 16 hours. To the reaction mixture were added trityl chloride (9.0 g) and triethylamine (3.0 g). The mixture was stirred at room temperature for 24 hours. The reaction mixture was washed with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous magnesiumsulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with 3% methanol/chloroform to give 7-(3-{2-[(tert-butoxycarbonyl)amino]ethyl}ureido)-2,3-dihydro-1-tritylimidazo[1,2-b]pyrazole (800 mg) as a solid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 16 hours
  3. stirringThe mixture was stirred at room temperature for 24 hours
  4. washThe reaction mixture was washed with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialThe organic layer was dried over anhydrous magnesiumsulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on silica gel eluting with 3% methanol/chloroform

Sources & evidence

ORD record
ord-cfddb53af54b4cd79ff92f01e9bb4093
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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