1,1'-Carbonyldiimidazole → HCID 21904590, compound

HRID 1247794Notes

Reaction equation

HRID 1247794 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[C:13]([O:17][C:18]([NH:20][CH2:21][CH2:22][O:23][NH2:24])=[O:19])([CH3:16])([CH3:15])[CH3:14].C(N(C(C)C)C(C)C)C.S(=O)(=O)(O)O.[NH2:39][C:40]1[CH:41]=[N:42][N:43]([CH3:46])[C:44]=1[NH2:45]>C(Cl)Cl>[NH2:45][C:44]1[N:43]([CH3:46])[N:42]=[CH:41][C:40]=1[NH:39][C:1]([NH:24][O:23][CH2:22][CH2:21][NH:20][C:18]([O:17][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:19])=[O:2]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 15610443tert-butyl N-(2-(aminooxy)ethyl)carbamateHCID 219045711H-Pyrazole, 4,5-diamine-1-methyl-, sulfate (1:1)

Product 1

HCID 21904590HCID 21904590, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1,1′-carbonyldiimidazole (973 mg) in methylene chloride (10 ml) was added O-[2-(tert-butoxycarbonylamino)ethyl]hydroxylamine (1.11 g) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. To the reaction mixture were added N-ethyldiisopropylamine (1.28 g) and 4,5-diamino-1-methylpyrazole sulfuric acid salt (1.05 g), and the mixture was stirred under reflux for 4 hours. The reaction mixture was washed with brine. 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 10% methanol/chloroform to give 5-amino-4-(3-{2-[(tert-butoxycarbonyl)amino]ethoxy}ureido)-1-methylpyrazole (255 mg) as a solid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred
  3. temperatureunder reflux for 4 hours
  4. washThe reaction mixture was washed with brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on silica gel eluting with 10% methanol/chloroform

Sources & evidence

ORD record
ord-c21ab3d7f81d4f3c92a5c6a45587a20f
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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