Triethylamine → HCID 178481869, compound

HRID 1247779Notes

Reaction equation

HRID 1247779 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[N:10]S(C(F)(F)F)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(=O)(=O)(O)O.N[C:32]1[CH:33]=[N:34][N:35]([CH3:38])[C:36]=1[NH2:37].C(N(CC)CC)C.C(OCC)(=O)C>ClCCl.O>[NH2:37][C:36]1[N:35]([CH3:38])[N:34]=[CH:33][C:32]=1[NH:10][C:9]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[N:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 36945701,3-Di-Boc-2-(trifluoromethylsulfonyl)guanidineHCID 219045711H-Pyrazole, 4,5-diamine-1-methyl-, sulfate (1:1)

Product 1

HCID 178481869HCID 178481869, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,3-bis(tert-butoxycarbonyl)-2-(trifluoromethylsulfonyl)guanidine (22.3 g) in dichloromethane (100 ml) were added 4,5-diamino-1-methylpyrazole sulfuric acid salt (10 g) and triethylamine (33.2 ml) at 4° C., and the mixture was stirred at room temperature overnight. The reaction mixture was poured into a mixture of ethyl acetate and water. The aqueous layer was separated, and the organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo. The concentrate was poured into acetonitrile, and the resulting precipitate was collected by filtration and dried in vacuo to give 5-amino-4-[2′,3′-bis(tert-butoxycarbonyl)guanidino]-1-methylpyrazole (11.62 g).

Workup

  1. customThe aqueous layer was separated
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. additionThe concentrate was poured into acetonitrile
  7. filtrationthe resulting precipitate was collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-2712a3eda6524cefae95afae20296eb2
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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