Ethyl Acetate → tert-butyl {2-[(2-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino)-2-oxoacetyl)amino]ethyl}carbamate

HRID 1247817Notes

Reaction equation

HRID 1247817 reaction equation
[O:1]=[C:2](N1C=CN=C1)[C:3](N1C=CN=C1)=[O:4].[CH3:15][N:16]1[C:20]([NH:21][C:22]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:19]([NH2:41])[CH:18]=[N:17]1.[NH2:42][CH2:43][CH2:44][NH:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49].C(OCC)(=O)C>CN(C)C=O>[CH3:15][N:16]1[C:20]([NH:21][C:22]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:19]([NH:41][C:3](=[O:4])[C:2]([NH:42][CH2:43][CH2:44][NH:45][C:46](=[O:52])[O:47][C:48]([CH3:49])([CH3:51])[CH3:50])=[O:1])[CH:18]=[N:17]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 1004391,1'-OxalyldiimidazoleHCID 187201N-BOC-ethylenediamineHCID 685167251-methyl-N5-trityl-1H-pyrazole-4,5-diamine

Product 1

HCID 86593408tert-butyl {2-[(2-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino)-2-oxoacetyl)amino]ethyl}carbamateYield 72.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1,1′-(1,2-dioxo-1,2-ethanediyl)bis-1H-imidazole (761 mg) in N,N-dimethylformamide (8 ml) was added 1-methyl-N5-trityl-1H-pyrazole-4,5-diamine (709 mg) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added a solution of tert-butyl 2-aminoethylcarbamate (1.28 g) in N,N-dimethylformamide (2 ml), and the mixture was stirred at room temperature for 27 hours. To the reaction mixture was added ethyl acetate (50 ml). After the precipitate was filtered off, the filtrate was washed successively with water, 5% aqueous citric acid solution and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crystalline residue was washed with a mixed solvent of diethyl ether and ethyl acetate and dried in vacuo to give tert-butyl {2-[(2-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-2-oxoacetyl)amino]ethyl}carbamate (823 mg) as a solid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 27 hours
  3. filtrationAfter the precipitate was filtered off
  4. washthe filtrate was washed successively with water, 5% aqueous citric acid solution and brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. washThe crystalline residue was washed with a mixed solvent of diethyl ether and ethyl acetate
  9. customdried in vacuo

Sources & evidence

ORD record
ord-1185d0e06a834749af5f3347f554930d
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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