Chloroform → N-([1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]methyl}-N-[2-(tritylamino)ethyl]guanidine

HRID 459653

Reaction equation

HRID 459653 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[CH2:8][N:9]([CH2:27][CH2:28][NH:29][C:30]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:10]([NH:19]C(OC(C)(C)C)=O)=[N:11]C(OC(C)(C)C)=O.[C:49]1([C:55](Cl)([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.C(Cl)(Cl)Cl>N1C=CC=CC=1>[CH3:7][N:6]1[C:2]([NH:1][C:55]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[C:3]([CH2:8][N:9]([CH2:27][CH2:28][NH:29][C:30]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:10]([NH2:19])=[NH:11])[CH:4]=[N:5]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 6456Trityl chlorideHCID 68519459N-[(5-amino-1-methyl-1H-pyrazol-4-yl)methyl]-N',N''-bis(tert-butoxycarbonyl)-N-[2-(tritylamino)ethyl]guanidine

Product 1

HCID 86760459N-([1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]methyl}-N-[2-(tritylamino)ethyl]guanidineYield 81.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-[(5-amino-1-methyl-1H-pyrazol-4-yl)methyl]-N′,N″-bis(tert-butoxycarbonyl)-N-[2-(tritylamino)ethyl]guanidine (1.84 g) in pyridine (10 ml) was added triphenylmethyl chloride (0.94 g), and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added chloroform (50 ml). The mixture was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with 3% methanol/chloroform to give N′,N″-bis(tert-butoxycarbonyl{-N-([1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]methyl}-N-[2-(tritylamino)ethyl]guanidine (1.60 g) as a solid.

Workup

  1. washThe mixture was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogencarbonate solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with 3% methanol/chloroform

Sources & evidence

ORD record
ord-f72b8e94ca8348b2b6cd4309decc6194
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Linked notes

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