N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine → [3-methyl-4-((1S,4S)-2-methyl-2,5-diazabicyclo[2.2.1]heptan-5-yl)phenyl][N,N-bis(tert-butoxycarbonyl)]guanidine

HRID 1027979Notes

Reaction equation

HRID 1027979 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][C@@H:13]2[CH2:15][C@H:10]1[CH2:11][N:12]2[CH3:16])[NH2:5].C(OC(N[C:25](=[N:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[N:26]1C=CC=N1)=O)(C)(C)C>CN(C=O)C.O>[CH3:1][C:2]1[CH:3]=[C:4]([N:5]=[C:25]([NH2:26])[N:31]([C:32]([O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:33])[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][C@@H:13]2[CH2:15][C@H:10]1[CH2:11][N:12]2[CH3:16]

Participants

5

Reactant 2

HCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidineHCID 686333063-Methyl-4-[(1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]hept-2-yl]aniline

Product 1

HCID 68983667[3-methyl-4-((1S,4S)-2-methyl-2,5-diazabicyclo[2.2.1]heptan-5-yl)phenyl][N,N-bis(tert-butoxycarbonyl)]guanidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Compound (Da), 3-methyl-4-[(1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]aniline, (0.105 g, 0.6 mmol) and 1-(tert-butoxycarbonylamino(tert-butoxycarbonylimino)methyl)pyrazole (H) (0.186 g, 0.6 mmol) were combined in DMF (2 mL) and stirred at ambient temperature for 3 days. The reaction was monitored by LCMS. The homogenous reaction mixture was then diluted with water (20 mL), the solid precipitate formed was isolated by filtration, and purified by column chromatography (silica gel, CH2Cl2 then 2-5% MeOH in CH2Cl2) to give [3-methyl-4-((1S,4S)-2-methyl-2,5-diazabicyclo[2.2.1]heptan-5-yl)phenyl][N,N-bis(tert-butoxycarbonyl)]guanidine; LCMS: purity: 99%; MS (m/e): 460 (MH+).

Workup

  1. customthe solid precipitate formed
  2. customwas isolated by filtration
  3. custompurified by column chromatography (silica gel, CH2Cl2

Sources & evidence

ORD record
ord-38eeb20a7e6d454b97a722d7c0dcafb9
Source dataset
uspto-grants-2014_05
Patent number
US08735418B2

Reaction notes

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